I am wondering if it makes more sense to do it now while it is warm and just recheck the gear oil at the end just to be safe . This would mean the oil in the crankcase would be slightly contaminated from use, and would winter over in the engine and gear case, would that be ok
It makes no difference when you change oils and fluids, as long as you change them. Oil that has been in use is not “contaminated”, it’s just been subjected to the normal combustion processes that it will be regardless of time of year. Sooner or later the engine will have used oil sitting in the sump, so whether that’s in December or July makes no difference.
IMO guys worry way, way, way too much about engine oil. Run good oil, change it at recommended intervals, you’re good.
I also think the “risk” of getting water in the lower unit oil is overthought. If you have a leak that is bad enough to allow a significant amount of water IN, then how did you not notice that big oil stain under the lower unit from oil leaking OUT? All lower unit gear oil has tiny amounts of water in it from condensation due to temp changes. That doesn’t hurt anything, the gears and bearings are so coated with oil that there’s no way corrosion will take hold.
Do the maintenance when it’s convenient for you.