I think this will not be popular with some tenants as they aren't planning that far ahead? 

I was thinking of house hacking a multi-family.

I manage on Oahu in Hawaii and I would assume based on things that I have heard from other hosts and managers in CA that the conversation around regulation would be somewhat similar given that it is a highly desirable destination for both guests and investors in the STR space.Speaking only to what I have experience with here - there seem to be three types of zones that vacation rentals fall into - on one hand you have zones where they are illegal, and while it is possible to run and gun in these areas I don't think the risk is worth the reward if you get caught.

You would think too little regulation would be a good thing, right?

Im not positive....but the general rule I think is that you are allowed to have 1 VA loan at a time.  

@Kenya Williams - I think others have made great points.

B grade area and good schools.I think property 1 will be easier to get under list price but not sure of vacancy rate since it's a smaller town.

It exemplifies the visionary thinking and risk-taking spirit that characterizes successful real estate investing — the ability to recognize the potential of undeveloped or underutilized assets and transform them into valuable and productive resources.Today, the legacy of the Louisiana Purchase endures, serving as a testament to the transformative power of strategic investment and forward-thinking decision-making.

(And even if they think they have a good eye.) 

You would think!