Investment Info:

Small multi-family (2-4 units) buy & hold investment.

Purchase price: $300,000

Sale price: $400,000

This investment doesn't fit any of the categories available, but it uses multi...

I would design a home for each site (five unique but similar homes, not five cookie cutters or copies), line up my construction pricing and then market each home for sale pre-construction.

Any major leasing items that I should be aware of that are unique to San Francisco?

First and foremost, it's important to note that there is really no single right answer for your marketing decisions, because each of your decisions can only be made relative to YOUR unique objectives.  

The smartest thing is what works best for your unique investing situation.

What unique obstacles do apartments present?

It’s unique to say everyone has a story in Real Estate.

It’s a long term hold, very unique property that would work well as a vacation rental.

I'm currently in a unique situation.

Given that it sounds like you already work hard and have a nice family (profile photo), I would suggest allocating any additional precious income-producing time to something where you have unique skills, a competitive advantage and can maximize your hourly pay rate.