Hello!

My wife and I are jumping in head first into a new real estate plan and I'd love some advice on how to property structure our endeavor. We are going from a pretty normal living situation, to a MUCH more complicated one, and we'd LOVE your advice. We are additionally looking for a CPA, and we have already received some legal council.

We own a single family condo on the north shore of Massachusetts, and just purchased, with the help of my father, a 4 unit apartment building in the same city. Because of our mortgage conditions, we are going to be moving out of our condo, renting it out, and into one of the 4 units in the new building.

My father's conditions for assistance were a loan for down payment, along with funds for renovation work. He would like to see a 7% return on his investment, interest paid monthly, and his money back when we eventually sell or cash out refi (~10 years out).

Our current intentions are to live in the new building, rent out our primary, and short term rent the 3 units adjacent to our unit in the new building. I did manage hotels for ~7 years, and have some experience with Airbnb currently.

We are unable to place the new building into an LLC due to the mortgage conditions, so we are instead going to put it in a trust. We are also going to move our original condo into a trust. We also currently have an LLC set up for our short term rental operations which we have been already running out of our spare room in our home which will cease when we rent it out. In total we will have 1 LLC and two separate trusts.

All that said, I guess my questions are as follows:

-We need to set up an operating bank account for renovation work for our new property, should we set this up through the trust, through our existing LLC or just pay using our personal accounts? My father, my wife, and myself will all need to funnel money through this account to fund the project.

-We have been told about Umbrella insurance from friends. Should this be something we consider?

-Will my father be able to transfer money into the LLC/Trust account without it being seen as a gift?

-When the time comes to pay back my father, will we be able to distribute proceeds from the sale/refi as we see fit?

Thank you SO much, I know this is a bit of a wacko situation! So many things are changing for us. I want to use every resource possible!  I know advice varies on market, etc, but I appreciate anything and everything! =)