There are a lot of ways to crash and burn, so increasing the odds of succeeding long term should be your highest priority. you can always sell your local assets once you're comfortable managing rentals and ready for a market that better-suits your criteria. btw, kudos for being self-aware of your limitations.

However, San Diego is an extreme case.However rents increase fast in San Diego.  

With VRBO, strangely, it keeps recommending significant increases which isn't wrong.

Also, watch out for any litigation or construction issues that could lead to HOA fee increases down the road.Alternatively, you could consider a good deal on a single-family home or a 2-4 unit property.

Ditch the red rug, increase art and add dresser, bedside tables to bedrooms.

You can find SF properties that already have in law suites, garage units, etc, and now legally rent those, so it should increase the appraised value significantly.

Its a nice little cheat/loophole on the mortgage side that can help afford a larger home pice and increase your chances of getting a home or other loans.If you have any questions feel free to reach out I am always happy to help and go over the basics.

Throw in that you can dramatically increase the value of the property once you show consistent rent rolls much higher than when the space was used for LTR, and you have a big win. 

In most markets it is not a linear price increase.  

You are already paying rent, so pay it to yourself to increase cash flow and accelerate savings for the next investment.