I knew VA loans were assumable, but I had always heard it was only by another person who was VA eligible.

I am based out of NYC, but am currently active in the WNC market and I travel down quite frequently so would be interested in attending in-person events as well.

Personally, I don't like QB because it doesn't give me the info I want about cash flow.

Obviously paying interest on underutilized capital is sub-optimal but when factoring in the cumulative proposed transactional savings, the annual total interest cost could be equivalent or lower than the net of an alternative home equity line of credit on the same principal loan amount.One 'hack' could be to delay the actual closing of the DSCR loan until a quality purchase prospect is identified and/or near under contract.

just having a large liability insurance and a personal umbrella policy?

We've gone through and vetted the local vendors to make sure the person inspecting it isn't going to just "look for work" as this very common in these industries.

In my opinion, going there in person can help so you can get copies of what needs to be filled out and can ask for a step-by-step process.

Having boots on the ground with an STR can make or break the guest experience, as well as preventative maintenance and quality upkeep of your unit. 

So, answer the first two questions and I will try to give you straight to a point answer, with no judgment or meddling in your personal affairs. 

If this is for personal use then I'm not sure I'd entertain this idea.