Which reminds me that I should mention that I’m not opposed to living a not-so-luxurious lifestyle in the short run.

Welcome to BP and come on over to the Short Term Rental part of the forums.  

I would think transient room mates on renewable short leases would be much safer than bearing the brunt of San Francisco's LTR tenant laws.

This plays into the affordability issues for tenants by allowing them to live in nicer neighborhoods for less money, yet I get monthly revenue comparable to short-term rentals.I have also shifted my focus to buying better.

I’ve been hearing some chatter about large hotel chains lobbying significant funds to push for regulations or outright bans on short-term rentals like Airbnb.

Short Sales, Bank Owned, $/sqft, school district, days on market, etc.  

I'm trying to analyze my first property and not sure how to set it up to run the number using the calculator tools here. 2 of the units are successful Airbnb short term rentals, and the other two units are month to month rentals to existing tenants.

Any way to capitalize on this garage outside of just attracting higher rents once I move out and/or higher sales price if I decide to sell?

Short-term rentals are becoming oversaturated in certain markets plus anti-STR legislation is resulting in some of those properties also converting to long-term rentals.You already have the operations experience by self-managing.

Update: It looks like the county has appointed an 11 person short term rental committee to review the work, investigate more, and provide a recommendation and will be disbanded by November 30th.