Bourbon Real Estate

Fixer-Upper vs. Move-In Ready: What’s Actually the Better Deal? | Bourbon Real Estate

This week on Bourbon Real Estate, we crack open a Ben Holladay 1856 Bottled-in-Bond and get into a big question for home buyers: is it better to buy a fixer-upper and build some equity, or pay more for a move-in-ready home?

We talk about different levels of home renovations, what buyers are really looking for, big-ticket items like roofs, HVAC, windows, kitchens and bathrooms, and whether sellers should renovate before putting their home on the market.

We also get into inherited homes, renovation costs, ARV (as-repaired value), changing design trends, the “lipstick on a pig” approach, and how a buyer’s budget, lifestyle and willingness to tackle projects can completely change the equation.

Plus, we taste and rate the Ben Holladay 1856 Bottled-in-Bond, talk about Missouri bourbon, bourbon pricing and trends, and somehow end up discussing craft beer, distilleries and rum.

Timestamps:

00:00 – Bourbon Real Estate & Ben Holladay Bottled-in-Bond

03:08 – Tasting the Ben Holladay 1856 Bourbon

05:00 – What Makes Missouri Straight Bourbon Different?

08:25 – Who Was Ben Holladay?

12:39 – Fixer-Upper vs. Move-In Ready Homes

16:30 – How Handy Are You? The Buyer Factor

20:30 – What Home Updates Are Buyers Looking For?

24:40 – Bigger Outdated Home vs. Smaller Updated Home

26:40 – Which Updates Actually Add Value?

30:58 – Should You Renovate an Inherited House?

33:15 – The Hidden Costs & Headaches of Remodeling

35:20 – Should You Replace Your Furnace and AC Together?

41:07 – Renovating for Different Price Points

43:32 – Ben Holladay Bourbon Rating

47:34 – Bourbon Trends, Prices & Small Distilleries

49:38 – From Craft Beer to Craft Bourbon

This week on Bourbon Real Estate, we mix things up with a little bourbon competition, real estate trivia, and plenty of Southwest Chicagoland talk.

We start by putting three bottles — Blanton’s, Fiddler Wheated Bourbon, and Larceny Small Batch — into a Royal Rumble to decide which one gets opened. From there, we dive into the history, hype, and taste of Blanton’s, including Colonel Blanton, Warehouse H, the famous horse toppers, and its connection to John Wick.

Then it’s time for “The Burbs & The Bourbons,” a real estate trivia game covering towns throughout the Southwest suburbs, including Lockport, Lemont, Frankfort, and New Lenox. We talk about local housing, downtowns, old homes, new construction, schools, commuting, development, and some of the things buyers should actually consider when choosing where to live.

It’s part bourbon tasting, part real estate conversation, and part Southwest suburban geography lesson.

Pour a glass and join us!

TIMESTAMPS

00:00 – Bourbon Real Estate tries a new episode format

01:47 – Choosing the bourbon: Blanton’s, Fiddler & Larceny

03:50 – Blanton’s wins the Royal Rumble

05:25 – Blanton’s Bourbon tasting begins

07:45 – Blanton’s history, Colonel Blanton & Warehouse H

10:00 – Blanton’s, John Wick & Hollywood

11:50 – Is Blanton’s overhyped?

13:55 – Blanton’s price, availability & value

17:45 – Introducing “The Burbs & The Bourbons” trivia

21:00 – Bourbon trivia: Can you identify the bottle?

24:50 – More bourbon trivia

27:50 – Southwest suburb trivia begins

28:00 – Lockport, Illinois: history, housing & downtown

33:40 – Buying an older home: what buyers should know

35:30 – Old home updates, electrical, plumbing & maintenance

38:50 – Lemont & Southwest suburban development

40:55 – Frankfort: older homes vs. newer construction

44:40 – Frankfort’s downtown, Fall Festival & Old Plank Trail

46:45 – New Lenox: growth, schools & community

50:40 – Commuting, train stations & choosing where to live

54:35 – Suburban growth, housing prices & affordability

56:45 – Frankfort home prices & the Southwest suburban market

1:00:20 – Final Blanton’s thoughts & tasting

1:02:25 – Final bourbon verdict & would we buy it again?

Bourbon Real Estate: Russell’s Reserve 10 & What Actually Creates Home Value

What actually makes a house worth more money? Is it the kitchen? The neighborhood? The school district? A finished basement? Or is it just having really good landscaping?

This week on Bourbon Real Estate, AJ, Ben, and Tim crack open a bottle of Russell’s Reserve 10 Year Kentucky Straight Bourbon and get into a surprisingly deep conversation about what really creates value in a home — and what homeowners think adds value but may not add as much as they expect.

On the bourbon side, the guys talk about Russell’s Reserve 10, its 90 proof, 10-year age statement, 75% corn / 13% rye / 12% malted barley mash bill, barrel placement, the infamous “Kentucky hug,” and the newly invented “wood hug.” They also get into Wild Turkey, Jimmy Russell, Matthew McConaughey, bourbon during the vodka craze, and whether AJ is finally developing a bourbon palate.

Then it’s time for real estate.

The guys break down:

    •    What actually determines a home's value

    •    Why comparable sales (comps) are so important

    •    How location and neighborhood affect pricing

    •    Why school districts can impact value

    •    Train tracks, busy roads, airports, power lines, and other “location deficiencies”

    •    Why being near a train station can actually increase value

    •    The difference between a house that is an over-improvement for its neighborhood and one that fits the market

    •    How square footage, bedrooms, bathrooms, garages, basements and lot size factor into value

    •    Kitchens vs. bathrooms vs. major maintenance items

    •    Why curb appeal can make an immediate difference

    •    How buyers and sellers can look at a property differently

    •    When a relatively inexpensive renovation can create significant additional value

    •    Whether turning a loft into a fourth bedroom is actually worth doing

    •    And why price and value aren't always the same thing

There are also plenty of side conversations, questionable bourbon terminology, cemetery “location advantages,” power-line debates, igloos, and stories from years of working with buyers, sellers, investors, and appraisers.

Because at the end of the day, value isn't just about what you spent on your house — it's about what the market is willing to pay for it.

Grab a pour and join AJ, Ben, and Tim for another episode of Bourbon Real Estate — where real estate meets bourbon, and somehow nobody can agree on what “wood hug” means.

Bourbon Real Estate: Old Forester Statesman, Contingent Offers & The Great Real Estate Circle

What happens when you mix a bottle of Old Forester Statesman with three real estate agents trying to explain one of the most confusing parts of a real estate contract?

Things get complicated… fast.

In this episode of Bourbon Real Estate, AJ, Tim, and Ben crack open Old Forester Statesman and debate everything from its 95-proof kick and barrel influence to the infamous “Kentucky hug.” Along the way, they dive into the history of Old Forester, its connection to the Kingsman movies, mash bills, rickhouse temperatures, and why barrel placement can influence bourbon's flavor.

Then things get REALLY interesting.

The guys break down house-to-sell and house-to-close contingencies and what they mean for buyers and sellers in today's market. If you currently own a home and need to sell it before buying your next one, this episode covers the challenges you may face, how sellers evaluate contingent offers, kick-out clauses, inspection and attorney review, financing, appraisals, earnest money, and how far along a buyer's existing transaction really is.

They also discuss strategies for making a contingent offer more attractive, why sellers may continue showing a property after accepting a contingent offer, how buyers can work with lenders to potentially avoid a contingency, and why having an experienced agent matters when multiple transactions are connected in a “domino effect.”

And yes… there is a lot of confusion over who exactly is contingent on whom.

By the end, even Ben finally figures it out.

In this episode:

🥃 Old Forester Statesman bourbon review

🥃 95 proof, mash bill & barrel influence

🥃 Kingsman/Statesman movie connection

🏠 House-to-sell vs. house-to-close contingencies

🏠 How contingent offers affect sellers

🏠 Kick-out clauses and 24/48/72-hour provisions

🏠 Inspection, attorney review, appraisal & financing considerations

🏠 Buying and selling a home at the same time

🏠 Creative financing and ways to avoid a contingency

🏠 Why market conditions change how sellers evaluate offers

🏠 The infamous five-transaction “domino effect”

Bourbon Real Estate is where real estate, bourbon, and completely unnecessary arguments come together. Grab a pour and join us.

Bourbon Real Estate: Can You Spot a Good Real Estate Agent? | Blind Bourbon Taste Test

What do Booker’s, E.H. Taylor, Bowman Brothers, and Old Fitzgerald have in common? In this episode of Bourbon Real Estate, AJ, Tim, and Ben put them to the ultimate blind taste test—and discover that identifying bourbon is a lot harder than it looks after a few pours.

While the bourbon gets stronger, the conversation turns to an important question for anyone buying or selling a home:

How do you know if you're working with a good real estate agent?

The guys break down what buyers and sellers should look for when choosing an agent, including experience, communication, local market knowledge, responsiveness, preparation, and whether an agent is actually educating you—or simply trying to get a deal closed. They also talk about the potential pitfalls of simply clicking the “schedule a showing” button on Zillow, Redfin, or other real estate websites without knowing who you're actually going to be working with.

The conversation covers:

    •    🚩 Real estate agent red flags buyers and sellers should watch for

    •    🏠 Why you may want to find an agent before finding a house

    •    📱 What really happens when you click “schedule a showing”

    •    📊 How to evaluate an agent's experience and track record

    •    🗣️ Questions buyers should ask a potential agent

    •    💰 Why the highest offer isn't always the best offer

    •    📝 Buyer agreements and what they mean for consumers

    •    🔑 What makes a great buyer's agent

    •    📸 Why accurate MLS information and good marketing matter when selling

    •    🏦 Why the lender can be just as important as the agent

    •    👨‍👩‍👧 The role of parents and family members in the home-buying process

    •    🤖 Where AI may—and may not—replace the expertise of a real estate professional

And, of course, there's the bourbon.

The guys attempt to identify four bottles completely blind, including a 125.5-proof Booker's, and things get progressively more difficult as their palates take a beating. AJ surprisingly comes out on top, while Tim discovers that maybe trusting your gut is more reliable than trusting the bourbon marketing machine.

It's part real estate education, part bourbon tasting, and part three guys questioning every decision they've made after drinking high-proof bourbon.

Pour yourself a glass and join the conversation.

🥃 Bourbon: Booker's Small Batch, E.H. Taylor, Bowman Brothers & Old Fitzgerald

🏠 Topic: How to identify a good real estate agent—and the red flags to watch for

🎙️ Podcast: Bourbon Real Estate

What happens when you combine a bottle of Old Fitzgerald 7 Year Bottled-in-Bond with three real estate agents talking about the chaos of today’s housing market?

You get another episode of Bourbon Real Estate.

AJ, Ben and Tim crack open Old Fitzgerald 7 Year and talk bourbon, flavor, bottled-in-bond whiskey, and some seriously wild bourbon history — including Prohibition-era prescriptions, the legendary Old Fitzgerald story, and the infamous Heaven Hill distillery fire that created a literal river of burning bourbon.

Then we switch gears to one of the biggest challenges facing today's home buyers: multiple-offer situations.

Why are buyers still competing against multiple offers? How does low inventory affect prices? Does putting 20% down actually make your offer stronger? What happens when the appraisal comes in below the purchase price? And what exactly is an appraisal gap waiver?

We also break down:

• How buyers can make their offers more attractive without simply throwing more money at a house
• Cash vs. financed offers
• Earnest money and financing strength
• Flexible closing dates and post-closing possession
• FHA, VA and conventional financing
• “As-is” offers and home inspections
• Why buyers sometimes win the house… and then realize they don't actually want it
• Why the best offer isn't always just the highest dollar amount
• How sellers and their agents evaluate competing offers
• Why having a good real estate agent matters when the market gets competitive

And of course, we finish by deciding whether Old Fitzgerald 7 Year is worth the roughly $60 price tag.

It's bourbon, real estate, questionable financial decisions and a few Kentucky hugs along the way.

Pour yourself a glass and join AJ, Ben and Tim for another episode of Bourbon Real Estate.

#BourbonRealEstate #RealEstate #Bourbon #OldFitzgerald #HomeBuying #RealEstateInvesting #MultipleOffers #HomeBuyers #ChicagoRealEstate #ChicagolandRealEstate #KentuckyBourbon

Bowman Brothers, Buyer Agreements & the New Rules of Real Estate | Bourbon Real Estate
What happens when you combine a $35 bottle of Virginia bourbon, three real estate agents, and one very confused bourbon novice? You get another episode of Bourbon Real Estate.
This week, AJ, Ben, and Tim crack open Bowman Brothers Pioneer Spirits Small Batch Bourbon and dive into what makes it different from traditional Kentucky bourbon—including Buffalo Trace mash, copper distillation, Virginia aging, rickhouses, barrel influence, and the never-ending debate over what “smooth” and “flavorful” actually mean.
Then the conversation shifts from bourbon to one of the biggest changes in real estate: buyer agreements.
Why do buyers have to sign an agreement before touring a home? What does the agreement actually mean? Can a buyer cancel it? Who pays the buyer’s agent? Is 2.5%, 3%, or 3.5% really the “standard”? What happens when the seller offers little or no compensation? And what should buyers watch out for if they work with more than one agent?
The guys break down the changes that came out of the real estate commission lawsuits and explain how they affect buyers in Chicago and the surrounding suburbs—without the legal jargon.
They also get into:
• Why buyer agreements became mandatory
• How buyer-agent compensation actually works
• Whether buyers can negotiate an agent’s compensation
• What happens when a buyer works with multiple agents
• Open houses and unrepresented buyers
• Dual agency
• Retainer fees and buyer-agent services
• Why some buyers resist signing agreements
• Zillow leads, referrals, and “tire kickers”
• The difference between Kentucky bourbon and bourbon made elsewhere
• How rickhouses and barrel temperatures affect bourbon
• Bowman Brothers' Virginia history and Revolutionary War connection
• And, of course, the official Bowman Brothers rating
Bourbon of the Episode: Bowman Brothers Pioneer Spirits Small Batch
 Real Estate Topic: Buyer Agreements & Agent Compensation
 Focus: Chicago / Chicagoland Real Estate
If you're thinking about buying a home, already working with a real estate agent, or just want to understand what changed in the real estate industry, this episode breaks it down in a way that's actually easy to understand.
Bourbon. Real Estate. And the stuff nobody explains until you're already sitting at the closing table.

Welcome to Bourbon Real Estate! You never get a second chance to make a first impression—whether you’re walking up to an open house, or pouring a 100-proof Kentucky bourbon.

This week, AJ, Tim, and Ben are cracking open a highly sought-after bottle of Colonel E.H. Taylor Small Batch. While we rate the "Glug Glug" and dive into the wild history behind the iconic yellow tube (spoiler: it involves 1800s saloon pirates and tobacco spit), we’re also tackling one of the most stressful parts of real estate: Prepping your house to sell.

Ben puts on his behavioral science hat to explain the "100-Millisecond Rule" of first impressions, while AJ and Tim break down exactly what buyers are actually looking at when they walk through your front door. From the brutal honesty of curb appeal and fisheye photos, to the debate over big-ticket HVAC replacements vs. cosmetic kitchen updates, we’re stripping away the realtor jargon to give you the straight facts.

Plus, stick around for some hilarious detours involving tank tops, loose toilets, and dying of dysentery on the Oregon Trail.

In this episode, we cover:

• (00:00) The E.H. Taylor "Glug Glug" and our first tasting notes.

• (05:40) Fun Facts: Why does E.H. Taylor come in a yellow tube? (The father of the Bottled-in-Bond Act).

• (26:45) Moving from the city to the suburbs: Walkability, community events, and bike paths.

• (42:00) Real Estate 101: How to prep your house for sale (and why curb appeal matters most).

• (45:00) The ROI of Renovations: Should you replace your roof or just paint the cabinets?

• (54:15) Decluttering, smells, and the weird "ghosting" effect of burning too many candles.

• (01:08:15) The behavioral science of "Confirmation Bias" in real estate.

• (01:11:50) Final ratings: Does E.H. Taylor Small Batch get the official stamp of approval?

Whether you are stressing over listing your house, hunting for a great bottle of Buffalo Trace juice, or just want to hang out with some guys who don't take themselves too seriously, grab a glass and join us.

Hit SUBSCRIBE so you never miss an episode, and leave us a review to let us know what bourbon we should try next!

Episode 1: Welcome to Bourbon Real Estate | Michter's Small Batch Review & Meet the Hosts

Welcome to the very first episode of Bourbon Real Estate!

What do bourbon and real estate have in common? More than you'd think.

In this kickoff episode, we introduce ourselves, explain why we started the podcast, and share what you can expect in future episodes. Whether you're buying your first home, selling your current one, investing in real estate, or just looking for your next favorite bourbon, this podcast is built for everyday people—not industry insiders.

🥃 In this episode:

    •    Our review of Michter's Small Batch Bourbon

    •    What makes a great "everyday drinker"

    •    Beginner bourbon tips, proof, tasting, and common misconceptions

    •    Fun Michter's history and bourbon facts

    •    Why we're not bourbon snobs—and why that's a good thing

🏡 Plus, we discuss:

    •    Why buying and selling a home doesn't have to be intimidating

    •    What consumers actually need to know about real estate

    •    How the Chicagoland housing market differs throughout the year

    •    What to expect from future episodes featuring lenders, inspectors, attorneys, insurance professionals, investors, and more

If you've ever searched:

    •    What bourbon should I buy as a beginner?

    •    What is Michter's Small Batch like?

    •    How do I buy my first home?

    •    What should I know before selling my house?

    •    What does a real estate agent actually do?

...you're in the right place.

Pour yourself a glass, pull up a chair, and join Tim, AJ, and Ben as they mix bourbon reviews, real estate advice, and plenty of laughs along the way.

Subscribe for weekly episodes featuring bourbon reviews, real estate tips, market updates, home-buying advice, homeowner education, and conversations with industry experts.

Everyday bourbon. Everyday real estate. Real conversations.