@MIke Steuart I haven't done a lot in Mass. but my understanding is that if you have an investment property, and it's not owner-occupied, then if you pull a permit whoever pulls it must have the CSL (construction supervisor license).So if it's your investment property, and you don't live there but you want to do the work (or supervise others you hire to do the work) then yes you'd need a CSL to pull that permit - or hire someone who does have it.I haven't done an apples to apples comparison, but my understanding is that generally CA and HI are Democratic places with lots of rules and regulations - like Massachusetts.

Also talking with a credit union that is a portfolio lender, they usually don't have such of a strict box for lending requirements since they old loans in house and they do have loan down payment loans that aren't FHA.

Use Airbnb strictly?

We have been managing short term rentals in and around Bozeman since before they enacted regulations on them, and have close to 1,000 5 star reviews.

More likely then not, the seller is looking for a stronger offer becuase the guidelines to qualify for FHA are strict when accounting for the conditon of the duplex.

I see from your response some of the issues I was expecting to be the biggest barriers to entry: capital and regulations/time to get approvals.

You also need to survey the local regulations on short-term rentals if some were going to go that way and see if the area is for or against them, in general.

I am speaking strictly NOI / PP.

@Gerardo Waisbaum To be honest, with all the new regulations around documentation for cost segregation that has come out, I recommend having a professional do them.

Airbnb rules are strict within the city of Austin.