I only dumped my Capri 14.2 a couple times, and it was mostly intentional
The boat is NOT a dry boat, so I'd say 60 degree water is your limit. Otherwise it's wetsuit time. Just my take.
Once you've sailed the boat a bit, you'll get a handle on her limits... I recall being able to stand the boat on its side, and scramble up onto the side of the boat, and could sit there most of the day, in a chop likely not.
The widgeon isn't gonna be much better as things get colder... so that really shouldn't be a deciding factor (IMHO).
The Capri 14.2 will point upwind OK, if you lock that rope traveler down... it won't point like a keelboat, but you can definitely get it upwind against other boats its size... The rounder bottom won't have the rigid stability of something like a holder 14, but will be more even handed as the winds heel you over (round bottom, not hard chine).. The centerboard arrangement in the Capri 14.2 is good too, it kicks up when you ground (if)... where others are daggerboards, and are pretty unforgiving. Keeping the bungees elasticity is key, because it'll help pull the board down, as you release the cleats.
The cuddy isn't waterproof in these, and you can overweight the boat if you fill the cockpit... making it hard to flip back again. I created a lockable hatch for mine, later models (including the one you are looking at I think), had this as standard.
There used to be a Capri 14.2 association, and I am not so sure it still is kicking around (it got gobbled up with several other associations, I think one of them was the sunfish)... anyway there were lots of answers to questions in that forum... But its a pretty simple boat, that goes fast easily, points well, and is still pretty forgiving. It's NOT dry, and it's still NOT a keelboat, so you can and WILL capsize it. The trolling motor is a perfect addition to the boat, to get you out and started, and back at the end of the day.. it won't do much when the breeze is up above 12, but then you SHOULD be sailing in those conditions.
I can't recall anything else as big deals on them. I'd say if I had purchased the keel version of the same boat (and yes they make them as trainers), I'd likely have kept mine, and even still be sailing it.
An equivalent boat is the Precision 15, and 15k... also great little trailerables, that are still made.