My family made theirs in real estate (house hacking a private money funded 4 family when I was little) so two different philosophies.

If you are hiring a PM, then it's not a big difference either way, but if self-managing you don't want to go much bigger than you have been or you may not be able to do all the work.

Or do you mean 4 SFRs on that lot, which would be a different story?

How long it takes to be financially ready is different for everyone.

Basically, the further you get away from the city the more potential for cashflow, but you're also dealing with a different tenant base that may be tougher to manage.

I have done a lot of these for my own portfolio, but am wondering if the tax implications are different if we do a cash out refinance for this partnership LLC and then have to "distribute" the funds to the members. 

If cash flow is the main goal, there are many other markets to consider before San Diego.

Since you have built a lot of them, could you spare 15 min to share your perspective on the main pain points of land discovery?

Let me know if you were unable to download and I can email you a version in different format. 

Main Edge Properties, LLC in Mustang is one of my companies.