@Alexei Amelenko It would be difficult to put this into a easily written format so I will just post the link to https://www.bizjournals.com/louisville/feature/crane-watch which should give you a general idea of the market.

People traveling these days don't just want to get away to their rooms, cuddle, and watch Netflix, they also want to explore and have an outlet to be outdoors.

This guy sounds like a hoarder who spends all day watching television and hanging out with his cats.

It's unlikely any long-term tenant is going to like you using the residence below them for a STR, watching a parade of people come in and out. 

And if you included the property manager in your calculations, you could use them to ease your entry into REI, while watching and learning, without as many possibilities for mistakes.If it cash flows on 3 units, or even with you paying rent, then renting the spare bedroom and STR/MTR rentals are just a way to increase your income, or you still have the option to stick with normal renting, and add the others, as you feel comfortable expanding your skills.Good luck.

Watching the process, ESPECIALLY the sanding was not something I felt comfortable with.

It's easy to obtain, costs very little, and doesn't require additional, on-going effort to maintain.Whatever cookies or algorithm is on my computer and phone, every time I open up social media or watch a  YouTube video, Anderson Business Advisors pops up.

When I first started out I thought I could figure it out watching how-to videos online, reading books, asking questions in forums, etc.

I guess I've just watched too many friends and family members taken advantage of in the past that I don't like to present myself as one of those types.

If you are newer turnkey might be an easier option, but watch out how the rehab was done.