If I had to pay my cleaners on top of the loss income it would impact even more as my cleaning fees range from $100 to $400 depending on the property.  

What price range do you want to be in if you're going to take it down yourself.I wonder how all these deals will turn out.

And what is your price range and are you looking for turn-key properties or something along the lines of a "fixer upper"?

Next, your using limited visual range photos.

I’ve been interested in real estate for years and have invested as an LP in several projects, ranging from residential single-family homes to NNN properties and flipping.While I haven’t owned any property yet, I’m hoping to take that step in the near future.

Might be worth considering in areas closer to central san diego for more options especially if you want to be around $1M range.

@Bryce JamisonEverything I own is built in the 1900-1940 range.

Good points I try to target a price range basically a starter  home  that is affordable in  A,B area . 

It can range from simple touch-ups to more extensive setups, depending on your needs and budget.How Does It Help Me Sell My House?

So assuming your son has low debt, then he should be able to qualify for a house in the low $300K range.