To get a 3/2 with a pool in Naples you're looking at 550k+ in a decent area where a STR would thrive, in Cape Coral its closer to 400k+ depending where in the Cape the house is located. 

I’m also considering advising my tenant to look into Section 8 assistance, as it could help support their financial situation while allowing me to adjust the rent closer to market levels.

You haven't provided us with any information that would help us help you.My recommendation: do not sell a property unless you have a plan to invest it in another property that will perform better, or if selling will move you closer to your goals.If you don't have a firm plan, hold onto it until you do.

It is coming to market in our off season, should we wait closer to our peak season to release it so that we have the best chance for the most bookings in a short time frame? 

I quickly chose one of the first 'investor-friendly' agents I found, bought the cheapest duplex on the market, and only interviewed a single property management company.Looking back, I wish I had taken the time to connect with more local investors in the area and leveraged their experiences to help me avoid some costly mistakes.After two years, I sold that underperforming duplex and reinvested closer to home.

So you may find what seem like good comps 2-3 years out, but if there are closer comps this is what the appraiser is going to use. 

They sold two appreciated duplexes in Dallas and we turned them into 8 units in Mesa, AZ with higher cash-flow, and much closer proximity to Southern California.I'll add to your Phoenix "pros" list:1) Landlord friendly rental rules2) Easy evictions in < 30 days3) Rents are rising faster (on a % basis) than many other metro areas4) Low property taxes (and the property taxes don't sky rocket after a purchase as they do in CA)5) Very low vacancy and extremely high tenant demand.

You can keep it under control a little by keeping the grass constantly cut and nothing laying around the house on the ground..

It's called land of 10,000 lakes but MN has closer to 11,500 and that just lakes of 10acres+.

If your role is critical to the project's success, aim closer to 50-50.