And @Matt K., just reviewed the contract... there's a lot there but I think the content below covers it.... 

I’ve been interested in long term rental property investing for a while now and have worked out a plan of action that I wanted to get some feedback on.My wife and I would like to buy and rehab a property that has an “extra” guest/mother in law house on the property we could live in for the first year in order to take advantage of the easier funding on a 203(k) loan while renting out the on-site guest house as an STR before potentially transitioning to a longer term rental when we are ready to move out.

FHA loans, including FHA 203(k), are not restricted to first-time homebuyers. 

I think this really impacts product with deficiencies, where last year at this time they were being sold for near top dollar, they are now not even getting the time of day.

@Joshua WilsonI insured my triplex for 70 k just for the building It was 401$ per year total

Agreed with @Dan K. - assuming you're close to/in Boston proper and on transit, no shortage of roommates versus families here, and you wouldn't be limiting your prospective tenants too much.

Originally posted by @Jim K.

@Aaron K.

@Jake K.

@Jim K.