Unless the city was offering grants or something to incentivize it, it is a risky proposition. 

They originally wanted to do something more like Denver's Airbnb/STR law -- basically allowing it only in your primary residence.

Avoid urban cities and target vacation destinations/national parks.A lot of successful people are keeping their hot markets on the down low.I would focus on an area that has demand and has a good outlook for continuing to increase demand, and then try to find good deals in that market and trying to create something very unique.

I was temporarily living with my family until I found something to rent.

Begin with something manageable to gain experience and build your confidence. 

I dont know the dynamics of every community of the United States, but under 250k multi in a class A/B community that needs no work is something I have never seen (in recent times).

This kind of thing isn't something that you just get your toes wet with. 

I would use a Ring Camera or something to keep the security good on the place..Sounds like you bought cash, yes there are insurance companies/brokers that will write a policy..

I negotiate with tenants on the spot all the time, if they want something different than what I want, I don't reject them, I propose something to accommodate but of course, I get paid for the accommodation.

If this is something you are interested in, mainly because less competition, you should test out one or two and see how it goes.