There's a reason that people try to buy properties off-market and that is because you can find sellers who care more about terms than maximizing returns.So start with a conversation: you already presumably have some rapport since it's your landlord and you've spoken before.

I think we offer an awesome service, but we can't control what people do.

The Cleveland market would allow you to hit those numbers easily.

The key takeaway was timing...selling each property in a way that allowed him to hit the 45-day identification period without rushing into a subpar deal.In your case, with SFHs in Jacksonville and Ocala plus that duplex in Port Charlotte, I’d look at where each market stands right now and figure out if there’s a single buyer who’ll pay close to fair value for the whole set or if you might do better by splitting them up.

-If you can find the room in your floor plan for a pantry closet next to kitchen, that's a hit. 

I've heard people have had a great experience working with them!

People reinstate the loans and do loan modifications all the time.

Having more people liable for the lease is usually positive in my experience.

Quote from @Reeti Peshawaria: Hi, I'm in the process of learning about short-term rental investments and analyzing potential markets, but I’ve hit a major roadblock: understanding local regulations.

Unless you're in the right market, traveling nurses can be hit-or-miss.