wink294, your concerns on water temp in cold weather are valid. Depending on air temp getting cold not cool getting in the proper heat range of the plug should also be considered. The plug heat range will effct the heat transfer into the head. I"m not says go do it just considerr it. Any time you improve heat transfer jetting should be considered. This is no different then proper piston to wall clearence. IF a psiton is to loose in a bore the piston will reatain more heat. The tighter the bore the more heat transfer to the cylinder walls and a greater load can be applied ( more power). By installing water jackets and head you have a way to disapate the heat being transfered to the cylinder and the heat being wicks out of the heat thu the plug. As less disapation is required ( due to cooler temp) the
Engine require a differnt air/ fuel/ heat range. If ones looks in there manual this in indacated basicy by the jetting chart for alitude and tempature. As the temps drop I would recomend a longer warm up time to make sure all is well insde the cylinder. This is exspecially true as the Engine gets time on it because of the bore clearence. On big factor to going to a jackets cylinder and head from air cooled is the preformance one can gain from a tighter bore. If you over cool with a fat jet and cold plug you gain nothing and accualy loose power. How this effect the cylinder is leaving too much heat in the piston and could cold siezure it and increase ring ware. This could even lead to piston squareing ( deformation of the piston as it cools back down form excessive heat). The piston pin and skirt will reflect this on tear down if it doesent stick first. "H" has plenty of documentation of this and the efect. New bore and the ody looses compression. The skirts were scored and the pin was to tight in the piston and the rings were gone. But the crown looked good witha dark looking plug.
What this means is standard jetting spec for the ody are out for this set up and one must dial it in.