It is not necessary to put a boat away here in NYC. Last three winters were mild. It was quite possible to sail year around. Those sunny winter days with just a little wind can be best days to learn your new boat. In water storage can be actually cheaper than storage on hard, and you will get a perfect excuse to escape a family, get down to your boat, open engine compartment, do nothing and feel great entitlement. It takes a few weeks of just watching all those wires, hoses, ropes, several engine starting and shutting down and valve opening to get slight idea of the purpose. Do not waist a winter.
Boat condition is more important than the age. You are talking about 10 years old boats, they may be as worn down as 20 y.o. boat.
For simplicity of single handling and nice interior I'd vote for older Freedom.