Wardie,
Welcome to TCT. The club is lots of fun with a great group of paddlers. I'm one of the few who still paddles a canoe. Most members have gone to the dark side (kayaks)
I don't have any recommendations for canoe outriggers, but you might check with Coleman to see if they make something for rigging a canoe for sailing. Outriggers could affect how well you're able to turn a canoe or make it easier to get snagged in tree limbs that might be partly blocking a river channel...something to consider. I've seen canoes that have some type of foam glued to the sides to add stability.
Don't know the extent of your paddling experience, but her are a few things to consider based on your questions:
1. Consider kneeling in your canoe to lower your center of gravity. If your knees can't take it, try getting a thick pad or those kneepads used by workmen who spend time on their knees.
2. Use your paddle blade to give your boat stability. By reaching out over the gunwale, and placing your blade face on or slightly below the surface, you will add a fair amount of stability to your boat. Once you get a little more comfortable in your boat, you can begin to learn a high or low brace to help keep you from flipping. These terms may not mean much to you if you're just starting out, but here's You Tube clip for a low brace.
http://www.youtube.com/watch?v=fw-44B-FmE0
3. Learning the ropes of paddling in cold weather months can be dicey. Wetsuits and neoprene gloves and booties or a dry suit (very expensive) are very good ideas. However, if you do not have those items, I strongly recommend carrying a complete set of extra clothes in a dry bag. All that being said, don't let this scare you from the Chili Paddle....COME! It's a blast. You'll get lots of help from everyone.
4. I always carry my keys (two sets) and wallet with me in some combination of a pelican case, dry bag, and/or zip lock bags. And I always have one set of keys in a pelican case in a pocket of my pfd which I wear at all times while on the water. I NEVER leave those items in or near my car. Although I haven't heard of car break ins around here at paddling locales, they did happen in a few popular paddling spots in the DC area where I used to live.
Hope this helps a little. Looking forward to meeting you. See you on the river!
jp