I don't have any debt and I don't have kids or much going on outside of my 9-5 career. 

Superhost on Airbnb and Premier Host on VRBO.

I’ve spent months doing online learning, lots of property analysis, and meeting people.

Sold property with “wrap around” financing so that on the underlying note I was paying 4% interest and collecting 10% on the new note.

(Roth's being an exception.)CPA Tom Wheelwright has a chapter on this in his book Tax Free Wealth and agrees with what I just noted. 

I'm reviewing my rental property insurance after having gone through issues with the first ever claim on my current policy, which we're finding out has poor claims service and lacks ordinance or law coverage.

Not sure how you can convince all of them we are on the same team. 

Bringing in the line and buying a new stove?

We will lose out on $100k but get our cash out and the new investor will clear $100k by sitting on a deal for a year (while collecting rents).Does this seem feasible or something that would be attractive to an investor?

He sent me a message on LinkedIn.