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A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

After saving 15% for vacancies/maintenance and all other expenses, this property cash flows $23 p/mo and a 0.48% CoC ROI.  

The current tenants are month to month and not interested in buying, and the existing mortgage balance is assumable (3.65%) for qualified buyers.I know it's a great house -- and with the assumable mortgage -- a great buy for someone looking to save with current interest rates sitting as they are. 

You don't want to lose your rate on the house you are living in now unless you want to sell it so since that is an owner-occupied, you need to stay there and save up the 20 percent for the second property based on what you said.

While automation can help with data pulling, it’s those conversations and local market knowledge that ultimately give us the edge in making informed decisions.I really appreciate your thorough response.

A good condo board should be saving money for larger projects as they are known in advance (eg every 25 years you need a new roof). 

It will save you a ton of money upfront and you'll gain the experience to upgrade to larger deals.  

When you add that: "The downpayment and closing costs would be one large hurdle"; I can't tell if you can only afford to do this once (thus tying up whatever you have saved) or multiple times.  

and if you don't have enough money to house hack in San Diego... save up until you do.and if you want to move somewhere else, house hack there.