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.

Staying local and house hacking—especially now, before kids—gives you so much flexibility to set yourselves up for long-term success.Your financial foundation is super strong, and house hacking a quad sounds like an amazing first step for you two.

I am very involved in our local real estate investor association and agree that in this central Florida market there are an over saturation of STRs as well.

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

Look for a local credit union that can offer a cash-out refinance once the work is done, ideally with minimal seasoning.

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

In my opinion, the best "first step" is to find a local REIA to attend. 

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

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.

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.