I'd vote Tampa for most of the stuff you're looking for (great fishing/water sports, arts scene, and single women); but the airport is a slight drawback in terms of number and frequency of direct flights.
Overall, I far prefer TPA to MCO (ease of parking and getting in/out...even with TSA precheck, it's a minimum of an hour in lines, longer if you don't have it--and DO NOT underestimate how long this typically takes, they are chronically under-staffed and the lines are always ridiculously long).
No idea where you travel to the most, but Tampa has direct flights to pretty much all the major metros. NYC, Boston, DC, Chicago, LA, San Fran, Seattle, Denver, Dallas, Houston, Atlanta, etc. Number of flights per day/week is a bit more limited than MCO, but you'll be able to fly direct more often than you think.