Ultimately, I would recommend doing whatever you've communicated to the other person (regardless of if that is a friend of an "arms length" tenant) . . . if you said "no rent while it's deferred" or something like that, then roll with it. 

Has anyone if the short term rental game gone to these lengths or am I over doing it with this ?

This unit extends about half the length of the building.

There may be local special first-time homebuyer programs that she can apply for, but I believe most will require some minimum credit score and employment length.

I am just going to ask him to pay the rent for 2 months ( the length of the 60 day notice) and to let me show the property.

I've found a 4 plex that has piqued my interest. It's recently remodeled and vacant, but ready for renters. It has one 2/2, two 2/1s, and one 1/1. I've run analysis conservatively and it seems it will cash flow fairly...

Depending upon how much you are charging for rent and the length of your leases, Furnished Finder should be significantly cheaper than Airbnb or VRBO for both you and your tenants. 

Hi @Alan Brown, unfortunately I don't have time to reply at length right now, but you're right - Massachusetts landlord laws are likely the toughest in the nation on a state level.

If it sits vacant for any length of time, you will see your cash reserves deplete rapidly.If it were me, I’d stay put in your current home, relish in the equity you built without risking it, and invest in something that will generate cash flow even if moderate compared to your first option.

Also check with them on their "Loan Cap Rates" to make sure they can service you into the future.Problem 2- Going SBA, you will research whether a Home loan versus an SBA loan both interest rates and term lengths are comparable.