The tenant fails to pay their last month's rent and leaves the place needing new flooring and paint.

Maybe I’m biased, but I think you’d be crazy to leave Greensboro for Ohio. 

I'd also mention that the rents were raised because they were well below market value and still are below market value, so they've been paying less in rent for X years.I'd also explain if the floors get replaced, they have to move all of their stuff out of those rooms and leave it out until the new floors can be walked on.

You should be looking to BRRRR but understanding that you should expect to leave some capital in the deal nowadays.

Ive hired a more hands-on smaller PM that actually has recommendations and has already proven to be more effective; Ive got 2 paying tenants and one leaving cash-for-keys tomorrow.

This is just one persons opinion coming from my personal experience: The challenge I'd like to leave for anyone who wants to break your golden handcuffs of a 9 to 5: If you want a different outcome, you have to put in different inputs.

They may want something and ask, or you can offer to leave things for $$$. 

While I love short and sweet responses over novels, sometimes too short leaves out clarity.

But it still created trouble in the past when some tenants wanted to leave earlier due to a deteriorating relationship.  

Hi @Ellen Feiss I agree with @Ty Coutts that you should start with informal, friendly, face-to-face conversations with the tenants to establish rapport, especially as you have some lead time here before next April.People don't like surprises or having to scramble, so if you are able to let them know your plans in advance, if they are reasonable people they should appreciate the extra lead time.This is especially true if their rents are currently very under market - they will have sticker shock when they look at what other units are renting for, and have to spend more time finding a new unit (if you'll be asking them to leave).If you have to move into one of the units yourself, I'm surprised you (or your lender) didn't make it a condition of the purchase and make the seller have the unit vacant for you.Sooner or later in rental real estate, you will have to establish a relationship with an eviction attorney.