Rent from yourself

[Rob Cucugliello]

Trying to figure out a few things for a situation my girlfriend and I are in. It’s a great situation, but rather complicated and hoping for some guidance. 

We found an amazing 4 unit mixed use multi unit we want to live in. The "owners unit" occupies the 3rd and 4th floor and we would rent out the other three units, one of them being commercial. Since it's commercial on the first floor, we need a commercial mortgage. This means we need to buy under an LLC and not our personal. We'll also collect rent and pay expenses via our LLC and its new respective bank account(s).

Noteworthy, and Coincidentally, my gf will run her own business out of the owners unit we intend to live in. It will actually take up a sizable amount of the unit.

My question is, do we need to rent the owners unit from our own LLC? Do we sign a lease? Do we charge market rent? Or under? Or over market rent? Or do we just rent to her business and live there anyway?

Lastly, we own our current home. We will need to move out and do extensive repairs which will then end up being rented (a delayed brrrr in a way). So that will be vacant and having losses during rehab. Since that home is in my personal name, can I write off the losses as a “rental” which it’s intended to be but not quite yet? Do I need to do anything to ensure it’s possible to write it all off? I’ve never converted a primary to a rental before.

Anything else we should do, know, or consider? Again, we have so much to figure out, that any help and guidance is appreciated.