Hassle Free RE

90 - From W-2 to STR Co-Hosting: Maine Markets, Amenities, and Expansion with Matt Welch


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Welcome to Hassle-Free RE! Today, Dave Menapace and Will Van Wickler sit down with guest Matt Welch—a former CPG sales leader who left his W-2 to scale a short-term rental portfolio and co-hosting company across Maine. Matt shares how he and his partners built an owner-first management model, why certain amenities (hot tubs, saunas) outperform in specific markets, and how they’re preparing to expand beyond Maine.


You’ll hear the real numbers behind portfolio mix (owned vs. co-hosted), lessons from testing amenities in different geographies, and what gave Matt the confidence to make the leap from corporate to full-time real estate.


Whether you’re investing, managing, or considering co-hosting, this episode is a playbook for building systems, choosing the right markets, and growing with intention. Tune in now to learn how to balance guest experience, durability, and ROI while planning your next expansion.


TIMESTAMPS

01:05 – Will’s 50 deals

02:10 – Cape Cod hot tub ROI

03:14 – Sheets culture on Cape

04:04 – Best product, best price

05:25 – Guest intro: Matt Welch

06:13 – Early path into real estate

08:22 – From LTRs to STRs

13:21 – Co-hosting, owner’s mindset

16:05 – Maine markets they serve

17:51 – 33–34 listings overview

20:56 – Hot tubs extend season

21:57 – Sauna on deck test

23:20 – Leaving a W-2

28:27 – 2025: team building

29:05 – 2026: expand beyond Maine

31:52 – How to contact Matt


Connect with the Guest:

Website: https://daysawayrentals.com/

Linkedin: https://www.linkedin.com/in/matt-j-welch/


#ShortTermRentals #RealEstateInvesting #CoHosting #MaineRealEstate #Hospitality

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