Tibike -- Too bad about your wife's RA diagnosis, that can be rough going. My wife has had RA for over 10 years and some periods were tough. We now do some family rides together and she does sporadic gym workouts to try and maintain weight and strength. For the past several years, she has been very healthy with minimla RA issues and with some care she can ride a decent distance. She'll probably never do a century, nor be very fast, but it allows us to do 40 mile rides currently and probably more with increased saddle time. Its usually her butt that gets her rather than the fairly flat rides we do. I've never been in one, but those endless pools seem very cool. Hopefully, its near the bike cave so as you perfect your wonderful toys she can be swimming nearby.
As for clothing, I find this time of year and a similar period in spring to be the toughest. Usually in the morning I will wear a shortsleeved Alertshirt or a Target C9 shirt under a long sleeve t-shirt (again either Alertshirts or C9). If the forecast is for rain I will carry my rainshell on my rack for quick retrieval. If there is no rain but wind I will either wear my rainshell or a Walmart windjacket I have. The windjacket is a litle warmer, but I need to talk my wife into doing some mods to make it really good for biking. I'm thinking that adding pit zips to it will make it a great jacket. But since I don't really sew, I will have to rely on my wife's skills.
Since I'm still carrying around more than enough personal insulation I find that I can dress a little lighter than others on the ride. Legs are still my problem. I have a pair of tights, but since they are windproof there are times when they are a little too much. I think I need to look into other lightweight tights. In the afternoon I'm usually down to just shorts and t-shirt since the temps will be 15-20 degrees warmer. This time of year goretex socks and gloves can be nice for the occasional rain shower. To sum up my clothing choices in this kind of weather it is several lightweight, cheap wicking layers with a rain or windshell as needed. I find I can adjust fairly easily, but it means carrying a lot of extra stuff which can sometimes be a pain. It is simpler in full out winter when morning and evening are much more similar.
Cig -- I'd certainly buy a patch or two if you can find a manufacturer. Thanks for taking on the extra work.
No ride today as I recover from the cold my son gave me. I should be riding tomorrow -- hopefully with my son to school as we get back on track. By the way has anybody ever carried a trombone on a bike? I've got to take one in on Friday for my son's 1st music lesson, I'll let you know how it goes, but suggestions are welcome.