Where in Southeast Michigan do you sail?
Some tips for winter that may help:
I would agree with you on changing out the tramp shock cord line for some no/low stretch line, it will stiffen the boat up, when you lace it up next spring
Make sure you drain your hulls as completely as possible before storage.
If you store your boat out side: strip off your tramp,(your going to that anyway) all your lines, and wires, tiller/hotstick if you got one (make sure you put a wire tie or bolt in the tiller mount on the rudder crossbar to keep the inside reinforcement bar centered on the inside of the rudder cross bar). store that stuff inside.
2 reasons: It gives you a chance two look things over real good, and it keeps them out of the weather. It will keep snow from potentially damaging/stretching out the tramp, your lines from getting dirty, mildewing, etc. Your wires are optional, but I always take mine off, and will even now that my shrouds have black plastic/vinyl coating. Coil the standing rig wires all togeather, then the trapeze wires set(s) togeather as in groups, in a 2-3' circle and wire tie them up.
Get some armourall or F21 super pertectant from turtle wax
(vinyl, rubber, plastic polymer) and generously put on any plastic and rubber on the boat and Mast. It will put mosture back in them from the sun taking it out. I do this in the fall and spring, but once an off season works good too. I just spray it on, and let it soak in.
Its OK to be conservative about your sailing, it all comes as you are comfortable and as you see fit. When you go over, its extra work to get it back over, although it does'nt hurt to go over,to be able to work at knowing how to right it. If you go out in heavy winds, it requires real alert observation, decisive thinking and more aggressive action/reactions. It can tire you out quick, especially if your soloing it. Its alot more stress on the boat, and things can break. If in the future, you decide to, go out on the wire, it is best to make sure that your spouse can skipper the boat proficiently to come back and pick you up, if you fall off, and vice-versa. You can learn in lighter winds, with one of you counterweighting on the tramp. Be smooth and fluid on rudder movements no matter who is out on the wire, jerky rudder movement can and will make someone lose their footing, even if their stance is wide with slightly bent knees and they are not paying attention for sudden turning.
There's alot of youtube videos out there with some good instruction on sailing hobies, check em out.
I can't help you on the jib furler, but sometimes I wish I had that on my boat when it comes to rigging it. but then again, I do like battens in a jib.
I don't know what dealer you use, but I think his name is Rick, at Midwest sailing in Pickney, MI would definately be able to help you on that. He knows his stuff http://www.ms-pyc.com/home.shtml