Also, I have no experience in trades or homebuilding, both of which (in hindsight) would have been nice to work on.Any general or anecdotal advice would be much appreciated.

Generally the fees are going to be very rough on DSCR Loans of that size (as a percentage of loan amount) but probably no choice right now - the market for DSCR Loans under $100k is very small and less than $75k even smaller. 

In most cases, they are very young with no income, no credit history, no rental history, etc.

Remember to celebrate your milestones, no matter how small, and continue to learn and adapt as you navigate the ever-evolving real estate landscape.

My girlfriend has signed nothing and gave no consent to have her credit run.

I contested it after that date last year and was able to get it reduced by sending them a few comps of properties in the area, but I would have gotten a larger reduction if I called earlier. 

The owners may agree to carry part of the financing, but you won't need them to stick around to transition operations.After acquiring the properties and assets you wish, you would either run your own business, or part-out and resell some of the assets.From your post, it does not sound like parting out the properties is a viable path and where you admit to having no experience with vacation rentals or the resort business, you might want to explore purchasing the business with the current owners hanging around for a bit to help you get your feet wet.Regardless of approach, it needs to have legs to be worth pursuing.

If a house does have some rotten wood ( siding and trim around the windows and or doors , missing an appliance or two ( say there's no stove or dishwasher ) ......

Takeaway is having at least 1 medium term guest will yes have lower rent potential but less headache and helps stabilize income.Gross Earnings: $2,200Expenses: $75 supplies (we clean ourselves, takes 10 minutes, and it's right upstairs no biggie)PITI: $2,700We paid $800 including utilities and any little repairs needed to live here.When we move out, we expect to cashflow around $500 a month conservatively.

One that covers you at no cost if you are EVER audited.