My concern is that a lot of younger, inexperienced and unsophisticated folks get fooled into believing that their hard earned money is going to "buy" property in these kinds of arrangements (i.e. believing they are not "throwing money away on rent") whereas throwing their money away on rent + even more money should the option fail is a better description of what is actually happening. 

This way, you can easily revisit details and pick up right where you left off.Avoid cutting corners to save money, as it often costs more in the end.

Am I not cut out for this?

I've stuck with the tried and true reasons I've heard to keep my search ranking high (quality photos, stellar reviews, updates to my listing) and that helps but in slow season, when I'm not willing to cut my rates as much as some of my competitors, it can be a ghost town.  

I would be very concerned about someone holding the 50k deposit for finish work at the end..

We have zero concerns of squatter in SWFL.

It was a huge investment, but it cut the electricity cost by the full 2K per/mo all summer.

It's this exact concern I have with dynamic pricing when I posted a few weeks ago about the RealPage lawsuit:https://www.biggerpockets.com/forums/530/topics/1225872-long...I'm sorry you're going through this.

My concern is the time it would take to grow these connections since I ain’t getting any younger! 

There's no clear-cut answer IMO, it's a personal decision.