It really just depends on what types of travelers you're attracting to your units.

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?

I think 5% is a pretty standard rate to estimate with, but beyond that you might be higher or lower depending on your approach to landlording. 

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

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.

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