The Landlord Diaries

FF112 Transforming Long-Term Rentals into Mid-Term Cash Machines: Darel Ison’s Proven Strategy


Listen Later

In this episode of The Landlord Diaries, we sit down with Darel Ison, a full-time professional who’s built an impressive portfolio of 19 rental properties spread across Ohio, Kansas, and Florida. With 7 duplexes, 1 triplex, and several single-family homes under his belt, Darel has mastered the art of converting long-term rentals into lucrative mid-term rentals.

Starting his journey in 2002, Darel's success isn't just about property accumulation; it's about strategic portfolio management. Discover how he’s transformed 4 of his properties into mid-term rentals, driving 85-90% of his bookings through Furnished Finder. Darel shares actionable insights into maximizing rental income without expanding your portfolio, by tapping into the mid-term rental market.

Key highlights include:

  • The strategic shift from LTR to MTR
  • Insights on managing out-of-state properties
  • Essential tips for property improvements and tenant communication
  • Leveraging tools like KeyCheck & Worry Free Waiver



In this episode...

0:00 Intro

2:30 Darel’s W2 & investing goals

3:20 The journey to 19 doors

4:00 Darel’s current focus: portfolio improvements & increasing profit

4:20 Darel caught every Bigger Pockets episode up to 600!

5:20 Struggling with tenants in your LTRs? Consider MTR

7:00 Host Katie Lyon’s investing goals for her kids & family

9:45 The difference in LTR & MTR tenants from Darel's experience

12:15 Not getting bookings? Tune in now.

15:00 Stay active in your Furnished Finder account

17:40 Want marketing feedback? Tag your Furnished Finder listing in the comments

18:15 Moving your first LTR to MTR

21:00 Fill your MTR gaps with STR stays: Darel got his normal rent in 4 nights

26:10 The revenue difference between LTR & MTR

31:35 Working with your contractors as an out of state property owner

35:35 Digital lock tips: which locks to buy, which to avoid, do not disturb feature & how they integrate with your channel manager

39:25 KeyCheck provides peace of mind throughout your MTR booking process

40:10 Travelers & landlords alike trust KeyCheck tenant screenings

42:00 KeyCheck makes splitting payments easy for travelers sharing a home

43:55 Worry Free Waiver: protect yourself & your guests

50:20 3 ways to present Worry Free Waiver to tenants

52:15 A separate pet guideline comes in handy

58:30 Incorporating QR codes & virtual tours into your real estate marketing

1:01:55 Finding strong multi-family deals on market

1:03:35 When your getting out bid over & over, change your strategy


  • Furnished Finder’s Worry Free Waiver
  • Darel’s Listings on Furnished Finder
  • Katie’s Lighting Product


SEO Keywords:
Mid-term rentals, real estate investing, rental properties, Furnished Finder, portfolio management, property conversion, rental income, Bigger Pockets, real estate podcast, tenant management, digital lock tips, multi-family deals, property marketing, out-of-state investing, real estate strategies.

The Landlord Diaries is brought to you by Furnished Finder, where you can list your property for one low price and pay zero booking fees.

...more
View all episodesView all episodes
Download on the App Store

The Landlord DiariesBy Furnished Finder

  • 4.8
  • 4.8
  • 4.8
  • 4.8
  • 4.8

4.8

87 ratings


More shows like The Landlord Diaries

View all
BiggerPockets Real Estate Podcast by BiggerPockets

BiggerPockets Real Estate Podcast

16,771 Listeners

Rental Income Podcast With Dan Lane by Rental Income Podcast

Rental Income Podcast With Dan Lane

828 Listeners

Passive Real Estate Investing by Real Estate Investing with Marco Santarelli, Investor and Entrepreneur.

Passive Real Estate Investing

977 Listeners

Tax Smart Real Estate Investors Podcast by Hall CPA

Tax Smart Real Estate Investors Podcast

414 Listeners

BiggerPockets Money Podcast by BiggerPockets

BiggerPockets Money Podcast

3,069 Listeners

Real Estate Investing with Coach Carson by Chad Coach Carson

Real Estate Investing with Coach Carson

609 Listeners

Thanks For Visiting by Airbnb Superhosts Annette Grant & Sarah Karakaian

Thanks For Visiting

579 Listeners

One Rental At A Time by Michael Zuber

One Rental At A Time

141 Listeners

Real Estate Rookie by BiggerPockets

Real Estate Rookie

1,839 Listeners

Short Term Rental Secrets Podcast by MICHAEL SJOGREN

Short Term Rental Secrets Podcast

14 Listeners

BiggerPockets Daily by BiggerPockets

BiggerPockets Daily

331 Listeners

The Short Term Show by 8 Figure Airbnb and Short Term Rental Real Estate Investor Avery Carl

The Short Term Show

443 Listeners

On The Market by BiggerPockets

On The Market

894 Listeners

The BetterLife Podcast by Brandon Turner and Cam Cathcart

The BetterLife Podcast

844 Listeners

The David Greene Show by David Greene

The David Greene Show

688 Listeners