My local credit union did a free appraisal on my house, and there were zero closing costs if I kept the money out for 6 months. 

Specific bank policy as opposed to what you can actually do elsewhere.

Not a lot of value add, but if I had to choose something it was switching from a STR to a traditional rental and going from collecting zero dollars in rent to collecting 1500.

If you need more get an umbrella policy.

We ran into so many challenges, to name one, I had ZERO experience with doing renovations, sounds like a fairy tale but it honestly all worked out, I was patient and I really believed I could get it together and get the job done.

My risk tolerance is usually pretty decent, but given the stakes (of being unable to find alternative financing), I can’t seem to mentally let go of conventional lending options.The risks I anticipate are: 1) Credit score will drop with a lot of activity in a short time (though I don’t know how much), 2) The properties are pretty rural, so appraisals could be low or lenders may offer lower LTVs because of the rural classification, and 3) Sudden market shifts could make lenders skittish about vacation rentals, making it more difficult to secure non-conventional lending.My questions are: 1) How confident can I be that I will be able to secure a DSCR loan?  

FYI, something to keep in mind... this is why low 6 figure mortgage underwriters, more or less, stay on the underwriting side, even if they're working 70 hours a week, with zero work-life balance, and having their souls sucked out.

I do not agree with there policies but it's how Airbnb works. 

Had a house I sold on a land contract that the owner could not afford to do the repairs on so we put a Loyds of London policy on it until he made the repairs. 

Be aware of the lender's policies with LTC and LTV though.