Or paying off my debt, while I provide them with a nice house to live in instead of an apartment. 

House was built in 2005 (I lived in this house and rented it out when I moved back to California). 

Then you own the LLC and can transfer the property into it.If you transfer the property into that LLC the way it is then technically you just gave your friend ownership of the house proportional to his ownership of the LLC.I'm not an attorney, so take that with a grain of salt.

The taxes here are high, but the price to rent ratio is exceptional and there is a huge demand for quality housing in certain neighborhoods.   

Win, Lose or Draw he's still in the records from your filing;-)Housing Court Judge, speaks to us at MassRealEstate dot net annually.

I was able to get a private loan which I used to purchase the house then I used my own money to rehab the house.

This means that your permanent residence is excluded (except if you are doing a house hack in which the part that is rented out is eligible for cost segregation).

We then purchased 2 houses for investment purposes.

As a community I think we should focus on helping people who have had their housing situation negatively impacted recover as quickly as possible.

@Joe Villeneuve around 300K of equity in the houseSell the house, take the equity, spend it or use it on your next house where you are moving to.