FIBI is a pretty good meetupI too was wondering about more local low key ones where you could just chat real estate and not get pitched deals by agents or syndicators

Quote from @Josh Ball: Recently bought a new condo that we have started a STR in.

@Amir GermanHouse hacking with an FHA loan is a smart move, especially in high-priced markets—low down payment, flexible credit requirements, and you can live in one unit while renting the others.

That is a what you/the investors need to be looking out for when buying.

Last year, I had a guest check in for a 5-week stay.

I own a two-unit multi family in Somerville MA.

They will need to verify you as a 3rd party authorized to discuss the mortgage, so your Grandmother will need to give permission - this can be done over the phone. 

I have a single family house and trying get it up and rented the contracter quoted me 39k for everything trying.

It should be a gray area or a guideline.

Good question, this trips up a lot of STR owners.