We put an emphasis on vacant prospects, those with separate meters and realistic balance sheets which when combined with the right financing terms and management can still produce a healthy and safe addition or anchor to a portfolio. 

If your target demographic (upper middle class/upper class/government workers) for your STRs are less impacted by these factors then that market will produce a better return now.7.

These rental apps do a great job of producing reports to track your rentals' performance, and output everything you need for tax filing.David OrrTax Modern

I would go with what produces the most cash flow at the end of the day.

Multifamily real estate investments, such as duplexes, triplexes, or fourplexes, have the potential to increase total cash flow as they may produce several sources of rental revenue from a single asset.

Introducing a fair negotiation on terms with (1) end price, (2) length of term and (3) cash up front could likely produce the results you BOTH are looking for. 

You can sell a few to pay off the rest or 1031 them into passive income.Any property you buy today should appreciate about 4.9% p.a. that's been US average (insert a % you believe is right, I believe Milwaukee may actually beat this number) over the next decades and your downpayment is leveraged 4:1, so that in itself produces a lot more equity over decades than you could ever safe up. 

I challenge you to find a single reputable source that shows San Diego residential RE has not produced outstanding ROI.  

@Dan Barth I would have a professional do the mold test that is certified to do so, these home tests are bogus and almost always produce some sort of mold.

most top producing resi agents avoid investors like the plague.