If it is kept in salt water, and maybe fresh, you will need to paint the bottom with antifouling paint. That will slow down, but not stop the marine growth from forming. I store my 28' boat in a slip in salt water and need to have the bottom cleaned every other month, and my diver would like me to have him do it every month. Other than that, I cannot think of any problems with keeping it in the water. A person a few slips away from mine keeps his 16' Catalina in the slip year round, and pulls up on the dock once a month to clean it himself, a bit messy but can be done. A 14.2 would be real easy to pull up and clean.
I see you live in T.O. I live in Oxnard and sail both Channel Islands Harbor and Ventura Harbor. If you get the boat we can sail together sometime. In fact, if you have never sailed a 14.2, I am willing to take you out on mine before you buy one.
I was out there just a little while back; I would love to catch up with you when I'm out again. Maybe take a boat ride with you and see how you handle your Capri.