NathanHey Nathan,A lot of the private/Hard money lenders that I work with do not require that, so depending on your strategy it shouldn't be an issue.That sounds like great idea though, it could set you up nicely to hopefully save up for a good primary residence.Would love to connect and talk through the strategies financially if you are interested!

Even with rates where they're at lenders require you to have a certain ratio on the payment of rent vs mortgage.

Most of the cash out refinance lender require me to move the property from my LLC to my name for the refinance, is that a normal operating procedure or is it a taxation nightmare to move it back to the LLC after the Refi? 

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.