In this episode of Homeowner Hotline, Steph sits down with Open House Austin’s Jennifer Carey to talk about her latest real estate win—a Wimberley property that’s part vacation home, part Airbnb moneymaker. Jennifer walks us through how she found the deal (spoiler: she almost skipped it because of bad listing photos), renovated it for under market value, and now manages it remotely while breaking even in year two. Read more about Jenn's journey here.

You’ll hear:

• How Jennifer’s 2010 first home purchase set her up for multiple investments.

• Why she chose Wimberley over other small Texas towns.

• The renovations that turned a dated house into a guest magnet.

• What it really takes to manage a short-term rental from a distance.

• Her tips for financing and setting realistic expectations.

Whether you’re dreaming of a Hill Country getaway or looking to scale your investment portfolio, this is a masterclass in turning a property into both a personal retreat and an income stream.

• Don’t judge a property by bad listing photos — visit in person to see true potential.

• Small-town tax rates can make a huge difference to your bottom line.

• Start small — Jennifer began renting just the studio before launching the main house.

• Guest experience is everything — from s’mores kits to handwritten notes.

• Break-even in year one or two is a win — especially with a property that appreciates and builds equity.

• Financing matters — know the difference between second-home and investment loans.

Book a Call with Jenn

Attend a How to Buy a House Workshop

00:00 – Intro & Jennifer’s preference for “Jennifer”

01:10 – First home purchase at 21 in 2010

02:57 – Pivot to investment properties & renting out her first home

04:31 – Why Wimberley and small-town scouting

06:26 – The property she almost didn’t see

07:43 – What she loved vs. what needed work

09:23 – Hidden value: two units on one property

11:14 – Renovations & budget choices

13:35 – The game-changing picture windows

14:44 – Staging, timelines, and first Airbnb listing

15:46 – Managing remotely & finding reliable cleaners

16:54 – Listing strategies & pricing control

17:57 – 2024 revenue breakdown

19:13 – Monthly expenses and cash flow

21:01 – Guest experience details & amenities

22:53 – Future upgrades: hot tub, game room

23:25 – Lessons learned and what she’d do differently

26:03 – Financing strategy and tax advantages

28:47 – Advice for aspiring STR investors in small towns

29:44 – Steph’s wrap-up and Hill Country real estate plug