I'm sure I'll fill in more info as I figure out what is pertinent.

Good life style.....About 10 years ago, I was looking trying to buy a condo there, but boy, every street was filled with "for rent" sign and I gave up at the time....

Short sales can get approved in 30 to 45 days if the agent is experienced and the seller co-operates with getting together required documents and filling out the financial forms.  

Not a matter of being legal but you must have the correct forms and know how to fill them out properly or you might make a huge mistake costing you money. 

A quick Google shows round-trips flight from San Diego over a weekend(ish) in mid-April around $300.  

It depends a lot on how high between your peaks and valleys if is more than say 1/2", most leveling materials are not design to fill in that much.

You should have in your expenses / P&L a line item for R&M (Repair and Maintenance -- basically toilets fill valve, A/C filters, dishwasher repair, etc.) and another for CapEx (Capital Expenditures - New Roof, New Water Heater, New Carpet, etc. 

And am I not supposed to back fill in that trench?

First, you did make the mistake by filling the suite one day earlier.

Once both units are filled it will cash flow well, but everything with this PM is a hassle and I don't feel they're really looking out for me.