After 25 months, If they can prove that they lived in the property for two of the past five years, they can sell it as an owner-occupied residence.

@Isaac TerryIn terms of it being worthwhile, just like most other markets out of state if the barrier or entry is too high where you live, the landlord laws are not favorable where you live, and you are looking for positive cashflow then Cleveland can be a good option.

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. --- They will offer to fix them in exchange for lower rent, but ask yourself, if the tenant has been living there for 25 years, why isn't everything fixed already?

I live in Kansas.

In my area these are rare so they are difficult to set market rent, and I imagine get a lot of wear and tear with a lot of occupants living there. 

However, I am thinking of having my parents who are retired living there part of the year and doing STR for the remainder of the time.

When your tenant stops paying and communicating, who will knock on the door to see if they still live there?

I'm originally from the area and have been starting to look at some properties there as I am living in New Jersey.

You do not have to live in the home in order to do that!