Quote from @Reeti Peshawaria: Hi, I'm in the process of learning about short-term rental investments and analyzing potential markets, but I’ve hit a major roadblock: understanding local regulations.

After you purchase your first property, I would use some of your savings to do a BRRRR or a flip and potentially a rental as well.

Also, ask your agent for recommendations—they often have relationships with dependable contractors.Look for areas with a mix of affordability and growth potential.

It checks all my boxes for potential.

It grabs attention, gives potential guests an immediate sense of what sets your property apart, and helps them imagine staying there.

Residential subdivisions, while potentially less complex, can be hit-or-miss depending on local housing trends and the cost of infrastructure development. 

Find a property that makes sense financially, in an area of potential growth, ANYWHERE in the U.S., and in your analysis account for slightly higher PM fees.  

But, I am not willing to commit to 50 years (if I am lucky) of never harvesting material equity from my rental properties at this time so that she can inherit potentially millions or tens of millions of 2074 dollars at stepped up basis.I plan to pay the tax man and spend some of my money at some point.

In that case you should get an attorney involved as encroachment would be a material issue that if known should have been disclosed both to the broker and to any potential buyer.  

For those with coverage, whether an occurance of it is covered would be based on how it occured and did/should you have knowledge about the potential for mold.