I check my "competitors" from time to time and there's a lot of empty slots in their calendars for the late spring and summer, just like mine.

I am currently house hacking a duplex with air bnb to cover our mortgage!

Hey @Caroline Knight I can't give advice for Chicago as I focus on House Hacking in Colorado Springs.

In our experience in Denver and Colorado Springs with midterms, it take 12-18 months for the extra income from it being an MTR to pay for the furnishings.

New Haven was ranked in the top #10 for Air DNA's best markets to invest in STRs for 2023!

I am wondering if there are any wholesalers, Florida or otherwise, who could tell me what they are currently looking for in or around Tarpon Springs, FL (About 30-45 minutes from Tampa and surrounding areas).

Journeys End and Silver Springs subdivisions. 

I shoulda bought in Colorado Springs 5-10 years ago before everyone else.

Listing in the spring helps.

But if you want to stay married, buy a place you both like, in a neighborhood you both like.This isn't exactly what you asked, but I see ambitious -- but skill-less -- first-time buyers in Denver and Colorado Springs want to take on a big remodel in the name of "value-add" because they read on here it's the best deal.