Mid-term is more likely to work in any market than STR, but I think you would be surprised at how well an STR could do if there are no other options like that in the area (think people's parents or friends coming in for the week(end)).I've seen a lot of people grimacing at the net-negative house hack (it's just a product of rates and low inventory in a lot of markets) and this is one option to try to recoup some of that loss.

Are you trying to hand your “friend” a 50% taxable gain that you’re going to keep?

AI tip 2: a friend of mine wrote an app (beta) for landlords to market themselves on a regular basis by soliciting reviews from tenants.

The app is user-friendly and integrates with popular CRMs, making it ideal for both beginners and experienced investors.

Saugerties and Phoenicia are pretty STR friendly as well.Hey Jonathan!

Correct me if I'm wrong but VRBO is very clunky and not very host friendly.

In my circle of family and friends, I will say that anyone that owns RE especially in CA has over at least several million in networth and they weren't high W2 earners (no surgeons or attorneys, but librarians, accountants, etc) but this takes years 15 to 30+ years..

I remember a friend of mine a few years back who tried something similar in the outskirts of San Antonio.

Hey friends, I'm an agent in Daytona Beach and I locking in my first short term rental listing.

It’s great to hear that you’re exploring real estate opportunities in Jacksonville, especially with your focus on Class B properties and military-friendly options.