We also watch "TV" on our own iPads in common areas, so there's no fighting over a TV or hearing their crap shows.I don't feel locked in my room.

My wife had recently gone back to school, and had become friends with a young lady who was doing cleaning on the side to bring in extra money.

Watch T-Bills rates go up, price adjusts down or appreciation slows, inventory increases.

The tenant is a sweet elderly lady with multiple health issues, limited mobility, and no income or ability to work; this would be devastating for her.

Based on that background, I'd say the following would be most applicable: Know the #s:- Accounting courses- financial modeling classes (now I'm doing deal syndication I wish I had taken more financial modeling courses) - specific real estate courses (as @Matt Devincenzo mentioned those CCIM courses have very good reviews) Connect with people: - public speaking (taking a stand up comedy class is like Public Speaking on steroids) - psychology classes and books (why do people do what they do) Be a good manager: - Business management (as you already mentioned) - Experience DOING or being exposed to it with an internship or job shadowing That said, my OVERALL advice is to find people who are doing these things and actually do it with them or closely watch them do it (then do it).

I like '70s and '80s pop culture, mid-century design, and watching pretty much any sport. 

The tenants watch me go down the check list, check boxes, make notes, and we discuss any findings. 

Like I said, I've been watching Sarasota real estate for the last 5+ years.

What should I be worried about or watch out for?

Also as I stated before it’s really fun watching someone get excited about a project and helping them learn.