Depending on the built in gain and how long you've lived there, you should be able to sell your current primary tax-free and roll any gains from that into your new primary residence, that is IRC section 121.Is there a set amount of time before you can move into the rental as your primary?

Depending on the ARV, I think you are better of using your own cash or getting a partner involved to finish the rehab and then cash out refinance with a conventional or DSCR loan.

The loan options and underwriting will differ depending on which path you choose.

Days on market are around 70 days on average, depending on the area.

The roof might be an expense depending on the specifics of your situation.I would also get a contract and invoice for the $8000 quote that notes $1000 payments being applied from rent monthly.

The rules for who may represent an LLC in a court depend on far more information than is present.

@Lucas SchlundI agree with @Ty Coutts that it depends on your risk tolerance and financial stability. 

It depends on your goals but I and many of my friends and clients started with house hacking and then used the equity to buy out of state.

I think it all depends where you are starting in your career.

(This, of course, depends on one's assumptions about future appreciation; the prospects of which I have my doubts.)