I've been saving for a while and would be able to afford a fairly new Ford Transit or Sprinter, although I would be spending a good portion of my life savings on this van.

We are wanting to transition these two properties into an LLC and are unsure about some of the specifics involved in doing so.  

@Josh Adams I also believe that multifamily is the way to go, for scale, and made the transition myself in 2018.

I'm also interested in 1 to 4 unit multi-families, possibly living in one of the units during the transition.

Transitioning/gentrifying.  

City of SD has actually gone well above State ADU guidance...any existing '2-unit' zoned property can get up to 7 total units....2 units per your zone allowance1 attached ADU 2 detached ADUs1 'bonus' ADU with the inclusion of 1 'affordable' ADUThe City code also clarifies that you do not have to build your remaining density before constructing the ADUs...and if your are in a Transit Priority area you can propose as many bonus/affordable ADUs pairs as you want.

Hope the transition to goes well!

The site is in transit priority area so technically I can utilize the ADU bonus density to build unlimited number of ADU.

@Dominique Palmer I currently have 10 SF houses but plan to transition into small multi family next.

If you decide to rent out your primary and transition to another house hack in one year, you'll be well on your way to your goal.