Simple post the deal in the local forums and indicate you are looking for a HM lender, 

If the system is supposed to be so simple, why can't a human walk me through it in a couple of hours. 

Then I would only offer a deal that was SIMPLE.

For example, if every lake cabin within 20 miles of yours listed on Airbnb seems super rustic and dated and "northwoodsy" (for lack of a better term), is there an opportunity for you to skew more modern in your STR design/style to help capture bookings with guests who are looking for that kind of aesthetic?

Forcing appreciation on this one. 15/30 balloon to capture better interest rate at 30 amortization.

Simple maintenance stuff.  

Rently has been working for me its pretty simple, the only Issue I had was with stupid people not following directions when putting in the code to open the lockbox, but I was able to walk them through it on the phone.

Which one (usually, and I understand it's not simple) has a better resale and long-term potential?

This is where a simple, old school paper application/word document will serve you well. 

Plain and simple.