Living in top unit and renting out the bottom.

Quote from @Sarah Kensinger: Boston is not STR friendly unless you live in the property.

. --- 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?

But this was an awesome opportunity for me because this is my first living situation where I will be on my own (and getting used to paying a rent/mortgage) but this will put my overall mortgage on a 400k house at roughly $2000 a month for the first year!

I have a client that bought a condo to rent after living there and the HOA ended up outlawing rentals.

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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.

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.