You will also gain valuable experience that you can leverage for other opportunities.Speaking from personal experience, I have several STR rentals in California (I co-own STRental Pros in Orange County, Los Angeles County, and Riverside County).

I actually had to get enough units where I could offer tenants multiple housing options when I purchased properties rented at way under market rates and then (an embarassing number of times) personally watch tenants that would "suffer" from a rent increase turn down smaller (but nicer places) or  nicer places in a less prestigious zip code (sometimes only minutes away) before I realized that I was hampering my ability to earn a living in order to subsidize the lifestyle choices made by a some random stranger that happened to live in a property I bought.

It's like a person who has serious stomach issues but refuses to go to the doctor because they're afraid they'll be given a terminal diagnosis.

Yes, if the person quit claiming had that right.

I use Travelers and had insurance on the landlord, dwelling and personal property level (because if the place is furnished by you, you have to have insurance on it) and they didn't cover anything.

Personally, I'd say find a market you want to go after. 

If it was me, I'd go there in person and DEMAND my money back, especially if it was misrepresented and they did nothing they were supposed to do for you!

I'm a rookie investor wishing to make his first rental investment for the purposes of house hacking. 

It's an exciting but complex decision, and I'm reaching out to this community to gain insights, advice, and maybe learn from personal experiences.Pros and Cons:I've identified several potential pros and cons but would love to hear your perspectives.

This helps them see it’s nothing personal, just math.Keep Learning: Laws about renting to people can change.