When I had my B&Bs we also included local restaurants and attractions in the packet of information which you might want for a STR.

C. and @Trevor Laramee I went through a local insurance company and was happy with the rate.

Having a reliable local team, including a property manager and a realtor familiar with the market, is the best way to avoid high-crime areas.If you’re leaning towards Richmond or have more questions about the market here, feel free to reach out.

But if they gov't changes to a 90 day minimum, you would have to operate as a 90 day rental or longer.And talking to local experts, if you want to own a STR on O'ahu, your safest bet is to buy a unit in a Condotel that is located in the "Resort" zone of Waikiki.  

Have you tried attending your local REIA's and real estate meet-up groups?

I’m Monica Bynum here a local agent in Memphis, Tn.

I would be self managing the property because I know the area well, have local connections to help out if in a pickle, and could get there in a day drive if need be. 

A local couple who’se combined income is 300K and who sponsored the family’s immigration to US is willing to be co-signers for the family of 5.I am thinking that Party2 will put more miles on the house and may be harder to deal with in case of any complaints or eviction, though I am not an experienced landlord so I am not sure what are the factors to evaluate or what all can go wrong?

I call them in-between because they are conferences, so not like your local meetups, but they are not truly "industry" conferences like NMHC, where you will meet primarily career, corporate multi-family people.Bigger Pockets Conference and Best Ever Conference are two that likely would cater to people more in your position.  

I'd suggest checking local Airbnb/VRBO data or using AirDNA to see occupancy rates and average nightly rates in the area.