I recommend you spend some time picking and getting to really know your market.

It appears he is on a course of actions that will not change.The pyramid scheme became obvious when the underlings started to reign down in the forums here, as many mentioned, where no one looks too kindly on SubTo, not knowing what they were walking into and not caring because they were looking for the "hungry" bros who would spend the $8,800 to get into the community and "share" deals.

Is this an amenity worth spending $$ on?

Do that before you spend any energy trying to kick him out.If he hasn't paid rent, you can call the police and have him escorted from the property. 

I took a few years out of work to take care and spend time with a family member whp passed, so I have only been working for a year now.

Multiple, billion dollar companies are investing heavy in our area, such as Intel, Google, and Amazon.

They aren't spending their own money, so they are less likely to take care of the rental or follow rules.

My thinking is this:1) Spend your money making the unit nicer, not investing in machines that will need service calls.

If you are looking for property in San Diego that is going to have good initial cash flow, you are going to either have to identify an obscure value add or expect to spend a lot of time and effort to find good off market purchase (most off market offers are not great). 

Considering the owner is currently distressed (not wanting to spend more to fix it up for listing on the MLS), I may be able to make it work at a reasonable price point.