Just focus on learning the local market, financing, and property management.

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.

It’s hard to manage remotely, so you’ll need someone local.

A good property manager can help with tenant screening, enforce lease terms, and handle evictions more efficiently if it comes to that.Require a Larger Security Deposit: Within the bounds of local regulations, a larger deposit can provide a cushion in case of damage or unpaid rent.Consider Rent Guarantee Insurance: Some companies offer insurance products that can cover lost rent in case of tenant default.

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

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

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.  

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.

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

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?