I do relatively well in my day job by today's standards but my hourly rate for self managing is closer to that of a surgeon. 

When clients come onboard, that process should be explained in great detail and by signing the PMA, you are agreeing with our standard processes and core values.Far too often that process is never fully explained and/or proper expectations are not set, hence new clients try to tell you how to run your business.

In fact assuming attached 4 small standard San Diego units, my maintenance/cap ex would be $1200 or almost 12% in your scenario.  

This requires an income that allows you to maintain your standard of living throughout your life.

I've found the easiest solution is to have a really strong banking relationship and then they will be able to provide non-standard offerings. 

That seems like an expensive roof - does it need to be completely torn up and rebuilt to hurricane standards?

And a drain within reach of the standard drain hose?

The standard process is already long enough, add on the scope of things and that's some significant time.

/ What is the standard in your market?

They have to meet modern codes and SEQUA requirements.. this is what stops building on lots that would not be buildable with modern subdivisions map act standards or modern zoning. in the hilly areas road widths and slopes will not meet Sequa so they stop building on those lots there are thousands of the lots scattered around LA county and these are the lots you see going to tax sale all the time.