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I just became a grandma (Nonna) and I love the idea of having one condo for each of my two children (they are next door to each other) to stay at with their children, in the future.  

Consequently, you must choose between immediate cash flow or future rapid rent growth and appreciation.

It will cost upfront but will pay dividends in terms of peace of mind in the future. 

Also, I was considering subdividing or CPRing the property into 2 lots, one property lot with the current retail building, and another property lot for the site of the future 6 unit multi-residential building.   

I think San Diego is a market that will always appreciate and even if you live there for a couple years and sell in the future you will be in the green.

I will say you absolutely have to make sense of your numbers and planning for future investment opportunity.

Consider buying a second duplex/triplex with 20% down and consider future financing.

As many STRs in the area, I have been dealing with cancellations and loss of revenue and will likely to do so for the forceable future.

In my area I'm allowed to rent it out that way but I don't plan to get separate addresses because I want to be able to have the flexibility to remove the doors I'm putting in should I ever want to sell it as a SFH in the future.