Real Estate Returns

Should you self-manage your rental property or hire a property manager? In this episode of Real Estate Returns, CPA Greg Seay sits down with Parker Touchton of Pinewood Management, who manages nearly 70 short-term, mid-term and long-term rentals across Northwest Arkansas and owns both types himself.

We break down what property managers really charge (8% to 10% for long-term rentals, 20% to 25% for Airbnbs), the hidden costs of self-managing a short-term rental, the red flags to watch for when hiring a manager, and how your property manager's hours can make or break the short-term rental tax loophole.

In this episode:
✔ Property management fees for Airbnb vs. long-term rentals
✔ Why "gross vs. net of cleaning fees" changes what you pay
✔ Hidden fees to ask about before you sign
✔ What property should never be a short-term rental
✔ When to convert an Airbnb to a mid-term or long-term rental
✔ Short-term rental regulations in Bella Vista, Fayetteville and Jasper
✔ How your property manager affects the 100-hour material participation test
✔ The tax records your property manager should give you at year end
✔ How to decide when it's time to hire a property manager

CHAPTERS
0:00 Intro
0:43 Meet Parker Touchton, Pinewood Management
1:31 Why he started self-managing his first Airbnb
2:04 Property management fees: long-term vs. short-term
4:42 Why your property manager needs a real estate license
7:03 What Airbnb owners underestimate
8:27 What property should never be a short-term rental
10:22 Converting an Airbnb to a long-term rental
11:35 Mid-term rentals explained
12:50 Short-term rental regulations in Northwest Arkansas
15:08 How property management fees and repairs work
17:46 Hidden fees to ask about
19:51 Red flags when hiring a property manager
21:37 What makes a great (or bad) owner
24:33 Who owns the Airbnb reviews?
26:20 Short-term rental loophole and material participation
28:35 Year-end owner statements and 1099s
30:36 Occupancy and tourism taxes
31:57 Advice for first-time rental investors
32:51 Self-manage or hire a property manager?
34:10 How to reach Pinewood Management

RESOURCES
Pinewood Management: https://pinewoodmanagement.com
Work with Cornerstone CPA: https://rei.cpa
Read the blog post: https://rei.cpa/blog/20261012

LISTEN ON
Apple Podcasts: https://podcasts.apple.com/us/podcast/real-estate-returns/id1640330438
Spotify: https://open.spotify.com/show/4sUygCOxAzBg9Rc6nCLbgt
Subscribe on YouTube: https://www.youtube.com/@reicpa/

Real Estate Returns: where the returns you earn meet the returns you file.

This video is for general educational purposes only and is not tax, legal or investment advice. Consult a qualified tax professional about your specific situation.

#PropertyManagement #RealEstateInvesting #ShortTermRental

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You can do everything “right” with an Airbnb and still feel that stomach-drop the first time your listing sits unbooked. Callie Anderson felt it too then her first booking hit within 24 hours, and that one moment pushed her and her husband from “maybe we should” into building a real short-term rental portfolio in Northwest Arkansas. We talk through what actually drove their demand near Beaver Lake, why they stayed local, and how being hands-on changed both their control and their profit.

We get practical about operations: how a clean, modern look shows up in photos, how small guest comforts like soap and snacks earn better reviews, and why hot tubs are both a booking magnet and a maintenance grind. Callie shares what self-management really takes, from weekly check-ins and stocking to managing cleaners, screening guests, and handling the occasional nightmare scenario like a last-minute discount guest who leaves a huge mess and then asks for a late checkout on a same-day turnover.

Then we shift into the tax strategy that made her say, “Let’s do it again.” If you self-manage and meet material participation, a short-term rental may open the door to cost segregation and bonus depreciation, turning decades of slow depreciation into potentially large first-year deductions. We explain the basics in plain English, why it mattered for their income, and how it influenced their plan to keep scaling toward five homes by 35.

If you’re thinking about buying your first short-term rental, or you already host and want a smarter tax plan, listen through to the end. Subscribe, share this with a friend who’s house-hunting, and leave a review with your biggest Airbnb question so we can tackle it next.

Links:

Blue Pine On Beaver
https://www.airbnb.com/rooms/786289620436693246

Modern Getaway | Walk to Beaver Lake + Hot Tub
https://www.airbnb.com/rooms/1513249977987503831

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Most people hire a real estate agent thinking the job is showings and signatures, then get blindsided by how emotional and high-stakes a home sale really is. We wanted to pull back the curtain, so we sat down with Katie Hendrickson of Keller Williams to talk through what actually happens day to day when an agent is doing the work well and why “hard conversations” are often the real product.

We get into negotiation, communication, and the contract realities that keep buyers and sellers protected, including how commission really works and why there has never been a universal standard commission. Katie explains how MLS changes and better transparency are pushing healthier client conversations, then shifts into what she’s seeing right now in the Northwest Arkansas real estate market: longer days on market, more price reductions, buyer leverage returning, and the pricing strategy that can still create demand when the market cools.

From there we go practical and investor-focused. Katie shares how she uses real estate marketing to increase visibility, where AI helps with listing descriptions, virtual staging, and even softening tricky messages, plus what makes a short-term rental or Airbnb perform in areas like Eureka Springs. We also cover renovation ROI using the cost vs value report, why pools rarely pay back on resale, how a 1031 exchange can go smoothly with the right qualified intermediary, and the inspection issues that most often blow deals up, with roofs high on the list.

If you want clearer strategy for buying, selling, or investing, subscribe, share this with a friend who’s moving soon, and leave a review with the biggest takeaway you’re going to use next.

Helpful links:

https://www.jlconline.com/cost-vs-value/2025/west-south-central/fayetteville-ar/

https://sellingarkansas.kw.com/

https://blinq.me/Z1Q1lEW9ztA1HrjElPiQ?bs=icl&s=s

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Most real estate advice sounds clean on paper until you try to close a deal with real life in the way. Greg sits down with Northwest Arkansas real estate agent, developer, and investor Darrel Donahew to talk about what the market actually feels like right now and what buyers, sellers, and investors keep getting wrong.

We start with the two biggest client “buckets” Darrel sees every week: families who are upsizing or starting a new chapter, and households combining generations with mother-in-law suites or multiple homes on one parcel. Then we move into the investor track, where many people are building from one to five rentals or turning a primary residence into a rental. If you’ve been told “there are no deals,” Daryl explains where opportunities still show up and why your relationships and agent network matter as much as the MLS.

The heart of the conversation is a memorable transaction involving a multi-home “family compound,” a value-add lot idea, lender hesitation, a fast pivot to listing strategy, and a closing process loaded with delays, signatures, and coordination challenges. From there, we break down practical takeaways: how contingencies slow deals in a softer market, what “binding with escape” means, why skipping third-party inspections is still a costly mistake, and how staging, decluttering, and curb appeal can help sellers stand out among thousands of listings.

If you’re planning a move to Northwest Arkansas, we also talk lifestyle-first research: walkability, nightlife, parks, golf, bike trails, and the different feel of Fayetteville, Bentonville, Rogers, Springdale, and Bella Vista. Subscribe for more Northwest Arkansas real estate investing and market strategy, share this with a friend moving to NWA, and leave a review. Which pocket matches your lifestyle best?

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Ever wonder what happens to your assets when you can't make decisions anymore or what happens to them when you pass away? We've got Natalie Perry, an attorney from Harrison LLP in Chicago, on board with us to make this daunting topic a cakewalk. She walks us through the concept of estate planning, unravelling how it's more than just setting up powers of attorney. Natalie, with her 25 years of experience, illuminates the intricate arrangements such as setting up trusts, emphasizing that estate planning is how you ensure your assets land exactly where you desire them to.

As we delve into the conversation, we uncover the significance of asset titling and the overlooked steps in the process. Natalie enlists the roles of executors, trustees, and agents, along with considerations for guardians of minor children. We traverse variations in estate planning across different states, discussing differences in taxes, distribution practices, and community property norms. An estate plan, as she explains, is not just a legal document, but a shield that protects from future conflicts and misunderstandings.

In the final leg of our talk, we discuss tax planning and the financial benefits that tag along with estate planning. Natalie shines a light on the federal exemption for estate taxes, currently perched at almost $13 million per person. She stresses the need to understand the intricacies of state tax laws and the potential benefits of annual gifting and putting money into trusts for children. Estate planning can be overwhelming, but with Natalie's insights and wealth of knowledge, it becomes an essential conversation about securing our future and assets. Don't wait until it's too late, tune in, and get planning!

How To Contact Natalie Perry
[email protected]
https://www.linkedin.com/in/natalie-m-perry-cpa-jd/

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Unravel the complexities of taxes and financial strategies with The Intelligent Taxpayer Podcast. Learn how to become a savvy detective in the world of tax codes, gain tax clarity, and keep more of what you earn. Stay updated with emerging tax laws, explore real-life case studies, and hear from industry experts. Subscribe now and take control of your finances.

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Ever wonder how your choice of business structure could be a game-changer for your enterprise? In our inaugural episode, we're throwing light on the big four - sole proprietorships, partnerships, C corporations and S corporations. Our host, Greg Seay., takes you through each type, discussing the pros, cons, and everything in between. From the ease of starting a sole proprietorship to the shared financial commitment of a partnership and the liability protection of C and S corporations, Greg paints a clear picture. But it's not all rosy - beware of potential pitfalls, like unlimited personal liability for sole proprietors and the complexities of disagreements among partners.

As we navigate the labyrinth of business structures, we also delve into the realm of Limited Liability Companies (LLCs). Greg stresses the importance of taking legal counsel here, given the complexities involved. And if you're feeling a little lost, don't worry! Greg's firm, Cornerstone CPA, is ready to help with a free tax planning consultation. This episode is more than just a podcast; it's your guide to making an informed choice about your business structure - a decision that can significantly impact your enterprise's future. Tune in for an enlightening conversation that could set you on the path to success.

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