If you're based in CLT I'd be happy to connect with you. 

Yes we were successful winning bidding wars 3 months ago using the family postcard technique;) Basically, we added a cute picture of our family along with our offers (which were based on conventional financing) and our “humanity” made us win over the cash offers.

If it was purchased cash you can do delayed financing immediately, but it would be based on your total capital invested not current appraised value. 

I’ve listed on FF and had a request for long term stay cutting into summer season and I comped it based on last summers revenue and declined.

We're all talking about the creative financing, asset-based lendings of the world right? 

You will generally get people who are more nomadic in nature. 

Based on your age & needs, you could consider a variable annuity (stock market) vs a fixed or deferred annuity (more like a long term CD). 

Coincidentally, I had this exact same question when renewing our local STR license as they've moved to a system (unfortunately) where the cost of the license is based on the number of bedrooms.

Given your focus on equity and scaling for future development, targeting properties where you can force appreciation through value add renovations seems like a natural fit.

My due diligence process was certainly tightened up after that deal and analyzing properties and understanding what things will cost is now 2nd nature to me.