Gaff Flicka
There is a considerable difference between a boat displacing 3,200 and one displacing 5,500. And while there's some performance difference between gaff and bermudan rigs, from a sailing point of view it's mostly when hoisting and reefing that you'll see any difference.
I've never sailed a gaff flicka, but I did spend a few hundred dollars checking one out very thoroughly; I too love gaff rigs and I've owned a couple of them. Based on my experiences with a boat somewhat similar in displacement and shape, a Benford full-keeled catboat, I can make some guesses.
It is likely that a gaff-rigged flicka will sail very well off the wind without an extensive off-wind sail inventory. It will sail well in reaches. It will not be a great performer to windward compared with racing craft, but just about the same as your Alberg 22 if the gaff is light or has an efficient preventer (the sheeting angle of the jib will mean you won't point quite so high, but the beam and mass will let you carry more sail longer.) If rigged with a topsail you won't need much in way of light air sails. If your boat is like the one I surveyed the gaff will be heavy, all spars will be wood, and no rig for the topsail. Wood spars will require tlc in St. Croix.
If your goal is BVI/USVI, a gaff flicka would be a good rig. Going uphill, well, it will depend on your patience and willingness to avoid pinching; you'll get there faster if you crack off.
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