I am a … well I call my self a master handyman my company name is One Man I am starting to / want to go big and help an investor with capital sit back and relax so that one day I can do the same as him .

Otherwise, I'm fine to stack cash, relax, and wait for things to change. 

This is to protect the Hotel del Coronado from losing business and to reduce turnover from any shorter-term vacation rentals - ensuring culture of the island remains quiet and relaxed.

So that might be a good avenue to consider - going to a retreat or being involved in a mastermind type program that gives you access to successful people over a several day period of time in a relaxed setting.  

I do think certain people are just wired to need their place to be exactly how they need it to be before they can relax (which I'm not defending, I know how frustrating that is as a landlord).

These growing states will have even more people looking for places to relax and play.

You easily get in trouble when you blow off your DIY tasks to have a relaxing weekend.

The restriction of the limited # of stays per year is my biggest concern by far.La QuintaSeems like the regulations are quite relaxed.

This is never a good situation.. what you can do is to work with her and tell her that she is equally laible and has singed a legal document that can be held in court of law... she should just pay her part of the lease value to get out... i would consider giving her some relaxation on payment to motivate her to pay, rather than going into a legal battle... then you can renegotiate with the other tenant if he is still staying there... eviction of course is the last resort and yiu can do it since one of the tenants have brwached the lease, which legally puts both ofvthem at breach, but eviction process is rarely landlord friendly and some tenants know this already...

Leave time for God, you, family, friends, relaxing, hobbies, etc.