No one can answer questions like this because the strategy depends on the investor's level of interest, financial framework, location, and many other factors.

The insurance and depending where you are at in upstate, the taxes are where it hits your pockets.

Of course, with all things, the answers to all these matters will depend on the circumstances.California tends to have more laws on the books and requirements and restrictions that it can be a good idea to form a CA LLC for out of state property so that you as a CA resident are covered, and to try to have your contracts fall under the purview of CA courts.

You can own more than one property with a VA loan, it depends on what your total allotment is.

Oh yeah.......depending on how trashed the place is, you can spend an easy $5-10k on demo , hauling and clean-up.

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

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 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.