A prior cost segregation study increases the depreciation taken during the owner’s lifetime, lowering taxable income each year.

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

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.

It has gotten increasingly frustrating to deal with inadequacies and complaints from my tenants as far as payment processing.

This is a very valuable skillset to have in your arsenal as an investor that can dramatically increase your net worth in a short period of time if the strategy is applied correctly.  

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

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.

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.

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.