That will free up your ability to use the FHA loan program again and not have to worry about red tape rules.This will also give you the opportunity to live with your Fiance' and test the waters. 

I would roll over some of my old 401k to the solo401k to start the funding.I just dont know how the k-1 negative ordinary income would flow into the Schedule C and how the cap gains at the end would flow? 

You site CASTLE Doctrine.....if the landlord has legally entered the residence, I would think this would not apply, not that I really want to test that.   

Is it tested in courts?

I am inspired by how everyone on this forum has gotten the ball rolling on their path to financial freedom through real estate but I am quite flustered & overwhelmed on where to even begin.

I for sure want to do the BRRRR method to keep rolling through properties and obtaining rentals but after sitting down I realized my main priority is to move out and House Hacking is the best way for me to do that.

We refinanced at a much lower interest rate and took out a HELOC to roll into our next investment.

The s*8t only rolls down hill for the tenant if you have to evict.

Might be better to sell and roll it into something without HOA fees.

If your roof was at end of life, I would agree that there is some advantage to getting the new roof rolled into your long term financing with the small side benefit of MAYBE a little higher value on the home.