You might want to consider adding another bathroom if possible. 

I've already renovated one of the bathrooms, and I’m planning to paint the interior, update the kitchen cabinets, possibly sand the wood floors, build a fence is a corner lot and increase the rent for the room since my tenant is currently renting the entire 3-bedroom, 2-bathroom house for $800 a month.

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

I’ve heard about partnering with insurance companies for displaced families, working with military personnel in need of temporary housing, and possibly connecting with other organizations that require mid-term accommodations.I tried reaching out to GEICO about insurance-related housing needs, but they didn’t seem to have a clear process.Does anyone have experience with this niche?

However, what I've learned is that for the most part, if most of your bookings are with guests that have a positive history (Airbnb/VRBO), your rates are competitive (to possibly slightly higher because you stand out, offer more, etc.), and you've made your House Rules clear, then don't sweat the small stuff.By that, I mean- you'll have guests who have 5-star ratings but can still leave a mess or damage (other owners didn't report accurately or it was complicated) but you have recourse via photo evidence (your cleaners, etc.) to ask for reimbursement (or use something like AirCover, etc.).

If your cleaners are trying to clean multiple units between 11 and 3pm, that is likely the only way it's possible.

It seems you would be most comfortable in Florida but if you're willing to move to other states, I would get out there if possible and talk to as many different people as you can with as many different opinions to get different takes.

Thankfully they're pretty good at helping to find the very small loophole or advise on how to work with it in the simplest and easiest way possible.

Real estate investing is more about taking actions and learn as much as possible along the way and not repeating your mistakes.

If you want to do STR, you want to get as close to the PATH or light rail as possible.