It's critically important to research not only the existing laws, but to talk to the city office to learn about UPCOMING regulations and general sentiment towards STRs.

Property Management team is critical

I think the critical question here is are these roommates strangers or not? 

definitely don't wanna buy before i take critical steps that would become a problem after i own the property and should have looked into earlier. thanks for any advice!!   

In the future I’ll add a lot more buffer in my renovation budgets, make sure there are contractors available to get started immediately, and question my agent much more about the exact state of the property before pulling the trigger on an offer (I’ll ask them to do as slow and critical of a video tour as they possibly can). 

The one I think is most critical and where most investors don't do their best is determining the scope of work.

It is critical to buy from a mom-and-pop owner and there are lots of things to look out for.

Hey @Mike Schorah Typically 1-2 times a year its good to scrub for things like sold houses, or just a general skip trace to ensure your records are the most up to date.With a list of 1000 or less this is not as critical, but when marketing at scale it can really become costly to have outdated data.

I'm hoping to get a ton more advice, some suggested reading material and articles, and possibly some constructive criticism from the pros here on BiggerPockets.

I'm on my third house hack here in East Oceanview, and it's been critical to scaling to where I am today.