I cannot argue with your sense of what looks right to you, since we all have our own personal aesthetic sense and when it comes to buying a boat, what matters is what looks good to you. But in terms of ease of handling, once you try a fractional rig, you might learn to avert your eyes.
The only trouble with the wing that I can see is that if you run aground, they are much harder to free. There was a time when this was a frequent topic around here. I spoke to a number of people with wing keel boats who also had owned conventional keels, as well as tow boat operators. While some wing keel operators ademantly denied that there was any problem freeing a wing keeled boat, the vast majority of wing keel owners and all of the tow boat operators that I spoke to said that wing keels are much harder to free when they run aground.
To me, here on the Chesapeake a wing keel is a deal breaker. If shoal draft is needed, and performance is even a remote priority either a shoal keel with a bulb or a shoal keel with a centerboard will generally outperform a wing keel, without the difficulty in freeing the boat in a grounding....