For overlay zones I often look at this site:https://scoutred.com/Overlays are important especially since your lot is in Point Loma so there is a good chance you are in the Coastal Zone, and the canyons are often considered "environmentally sensitive" land, both types of overlays often require additional processes for permitting your project. 

Some differences between SFH and MFH (4+ units):-you will need a licensed architect-you will need a licensed M/E/P engineer-you will need a civil engineer for the usual grading/drainage, plus consolidating the 2 lots and/or the condo split for the townhomes-there may be other consultants required for landscape architecture, environmental studies, etc.

However I do understand that there are a lot of other components that go into managing.. 

I recognize the debt to income component. 

What are big key components you view when making sure there is demand in your market? 

Buyer-  known, funding letter from bank, repeat or future repeat buyer, 1031 exchange, etc  Basically lay out the key components to a sale and use that as your model on why property offers are accepted or not. 

The ability of a real estate business to continue operating normally even when you are not present is essential to its success, as I have stated on numerous occasions.Recognizing your own limitations and the areas in which you may be the bottleneck is an essential component of individual development.

I have been approached several times to join EXp and like some components but dislike others.

It happened because my customers came to me when they saw I am really good at it.I've acquired over 1,000 apartment units for my own portfolio and I believe one component of my success is because I have my "PhD" in property management...my training is managing properties in the WORST area you can possibly imagine.

You may be able to defer tax consequences of a sale (ASK YOUR CPA FIRST) if you structure it right and he stays in.Then do a comp on a replacement prop (which he doesn't know) vs. staying with his prop (which he does know).