The people who bought in 2012 had it pretty easy and while they generally were the big winners they still could have ended up as losers if things changed for the worse.Regardless its really up in the air how the market will react to certain news and I think COVID showed that because despite a very uncertain future where most would think home buying would be on the decline, people are still buying houses because human behavior tends to react irrationally.  

But I thought about your idea a bit more and realized I would most likely be able to air bnb the place after I've lived in it a while (maybe even during) and could very likely break even on my mortgage or even more likely (and more importantly), I could make a profit.

I'm in St Pete, and an Air Force vet (Nav, working on CFI for fun in my spare time).

Then rest of lot graded so Zero puddles even after a fast 2 “ rain.Then downspouts getting ALL Exhaust water at least 5 feet.If you still have any moisture inside you may need interior drain tile and a sump pump around complete perimeter wallsTHEN think of Rebuilding walls in correct way with moisture barrier and air space.

My rental does not have central air and I require the tenants to provide their own window units if they want it (This is noted upfront before they sign the lease.) 

Ouch, that would give anyone air sickness.

I have 10 years in the Air Force.

We also charge a $300 security deposit, along with a monthly fee for animals and air conditioners.

The whole transferring Title bit is up in the air. 

Hello everyone! I am brand new to the investing world, my husband and I are looking for a vacation home on a lake in Michigan, Appx 2hrs from Chicago. I would like to rent it out via Airbnb while not in use. Any loca...