In my free time, I'm a wine/food guy who loves to travel. 

., travel nurses) especially in the Bay Area, who could give me some advice?

Logistically if the place where you invest most and the place where you live are easy to travel from and to, it is vey convenient

The idea of owning and managing vacation homes that provide memorable stays for travelers excites me.

She has her time back and travels constantly to visit her family.

If you are worried about fees and occupancy rates, I would suggest flipping back and forth between traveling nurses.

Here's a quick summary:Manchester: STR demand could come from business travelers, especially near Hartford.Canton: Lower demand unless near outdoor recreation areas.Southington: Strong option with year-round tourists (skiing, Lake Compounce).Bristol: Good potential with ESPN and tourist attractions.Berlin: May have less demand unless near major highways.Focus on properties near attractions or business centers to keep occupancy high.

I have a 4-unit property up in Cape Coral, FL that is currently wrapping up construction. I've been approached by a couple of sober living facilities and would perhaps prefer an independent living provider if possible...

You could invest out of state, which would open up different risks and costs (trusting your PM, additional travel costs to see your property(s) periodically, likely less personal market knowledge).  

He wanted me to travel with him and buy some of these deals.