It's probably pretty vague.If so, you're highly unlikely to win in court.Also, it appears you may be incorrect about your eviction assumptions.You state you, "found 3 forcible detainers".

After digging around I've come to the conclusion that for a small team with a small amount of properties you simply can't beat a free solution like Google Drive with Google sheets, docs.

Heads you win, tails you win.

As I indicated, you can simply look at the price to know this is true.

I do know the why and the goal, but sometimes I simply get scared by the risk.

Moreover, some private lenders may want to be a debt partner and not an equity partner where they are simply lending you the money and you pay a set interest rate just like a bank loan. 2.)

I could write a book on how to win the lottery and its the equivalent. 

Great design, Airbnb ready, I sold it like a business that earns 2,000 monthly, a win win Lessons learned?

With that being said, you can build a successful STR if you win on two fronts (to simplify it)The real estate side and the hospitality side (operations).The real estate side is buying a very good deal in a market that has a history of vacation rentals in my opinion. 

We simply need to find a lender willing to transfer the debt is our current thinking?