Massachusetts requires that *all* STR platforms collect both city and state STR occupancy taxes and remit them to the state monthly.

It requires patience, especially in the face of market fluctuations.

Find out what the requirements are for that driveway.

Choosing an FHA loan over conventional has its perks:-Lower down payment requirement: With FHA, you could put down as little as 3.5%, which could help you hold onto more of your $250k.

I have funds totaling around 20k for a down payment (100k home), however for my planned strategy I’d like to target homes at max 200k which should require a 40k down payment.

Not a lot of houses come my way on Zillow or my realtor that fit into my buy box requirements.

However, I will still be required to pay income tax on the income generated from my private lending activities.

AKA Work-ready.I purchased the home with an FHA loan, and my original contractor (as required by FHA otherwise I wouldn't have used one) underbid the contract not understanding the inflexibility of such a loan.

You're getting the desperate ones which is why you don't feel enthusiastic about the applications.

Banks will require that you hire a licensed contractor.