couple points
Having seen several trailers backed over the end of a concrete ramp, no amount of horsepower will help pull it back over the "end" I've even see one unlucky fellow who had that perception when he ask another with a one ton 4-wheel drive to help him.... He did, and promptly pulled the axle and springs off the trailer... One has no option but to raise the trailer, a major project that one will see often launching on some of the Florida ramps.
I've owned both swings and the wing I currently own, the wing is much stiffer boat than either of the swings. In fact I have yet to put the rub rail even close to the water. On the swings I could wash the windows and ship water into the cockpit at will...
Pointing; it's true the wing will not point as high as a properly rigging swing keel boat. But then that leaves all those boats that are "not" properly rigged... It would be a huge misconception to believe the wings won't point....

We've found there might be a 1 -2* difference. But the ride is totally different, I'm sure Don will agree.
You will find that those that own the early boat models seem to believe they have the "one" Those that own the "new style" believe they have the "one" (none so believe this more than those fellows I sail with who own the new style, "to them this is only model to own") Others like the MKII. These folks spend large amounts of time on the boats, I just spent 6 weeks with one of them, we both were very comfortable on each style boats. I can tell you the old style boat isn't the most comfortable (unless changes are made inside) for long term cruising. All models open many waters that won't be open with larger boats.
We sailed an area in the keys my friends could not sail with the 27 Catalina they own, in fact they could not even get the 27 into the marina we used to launch. (4' draft on the 27)
While in the beginning I didn't like the MK as well as I did the "old style" I owned for so many years. But I'm beginning to like it more and more... and the 6' 5" head room with the canvas on while at anchor makes a huge difference! But the choice is going to come down to you, no matter what we tell you.
I would encourage you to find a Catalina fleet introduce yourself ask about a sail on the different models, they all will have pluses and minuses.
It sounds like your interested in day sailing, if that's true you might want to limit your search to either one of the early old style boats or the sport model. The sport model has the early hull with the later keel hangers, but has a Capri deck. This makes getting around on the boat under sail much quicker and much easier.
Good luck with your search....