To be honest, between the anti-landlord legislation and propaganda that demonizes anyone who's a housing provider or developer, combined with a glut of housing units currently on the market that is causing me a ton of work to find good tenants for any given vacancy (think about that contradiction for a second), I'm really struggling with landlording at the moment. 

Our STR we use a PM and it is work (we tried doing it ourselves many years ago and we are fairly experienced PMs but this was too much work for our lives - we self manage around 20 LTR units if we thought it was not easy imagine less experienced PM).As @Aaron Friberg indicated before considering STR on Condo make sure that it is allowed in the complex.In summary, the rents are good but STRs in San Diego could have legislation curtailing them and STRs at the beach are not passive.Good luck

I suppose my parents did this for tax reasons but I am uncertain as to why. 

(I'm uncertain if that also included mortgage professionals, insurance agents, title company people, etc.?)

That's still illegal.Over time the "food industry" will eat its way up the "food chain" and take over the processed product categories one by one too, and for the same reasons.At a moments notice, if the federal government decides to play rough, all they have to do is pass some legislation (or just threaten) to revoke the charter of any bank that accepts money from any pot related bussiness. 

Hey @John ParshallAs others have mentioned, the current legislative landscape leaves the outlook on the viability of STR investments in SD a bit up in the air.However, as @Dan Heuschele stated, ensuring that the property is viable as a long-term rental will drastically reduce the risk associated with that uncertainty. 

When i am uncertain about a new property and the rents it will fetch, i put out a craigslist ad with the address and whatever pictures i can get my hands on and market it for the rents i want. you should know by the response in a couple of days if the rent is too high or low. 

If you are uncertain of the houses' roof, heating, wiring, plumbing, etc have them inspected.

I always tell my clients however, if you are considering doing a transaction that you are uncertain would be in violations to the rules, simply ask.

He is allowing me access to the MLS thru him but I’m uncertain what data is best to have in order analyze comps/potential deals.Here are some things I plan on asking:-Comps in my target area-Hot ZonesThings I’m unsure on:-What data I should prioritize without having a subject property to allow me to find potential deals-should I continually check in with him to record update data?