These wheels are easy to overlook going by the spec sheet alone, but these wheels are much better than the specs would suggest. They are super responsive and more comfortable than I expected, certainly not to the level of something with a 25mm internal width, but they handle rough pavement surprisingly well. The stiffness is really impressive, I'm able to put out about 1000 watts in short bursts and I don't notice any lateral flex or spoke deformation at all. They hold air better than any wheels I've previously used, I think that is partly due to the GP5K AS TR tires, but Shimano definitely made this wheel the right way. These are probably the most stable wheels in crosswinds that I've ridden and they hold speed nicely as well. Shimano might have a more modern design in the works at this point, but these wheels are still really solid performance wise and the ride feel is amazing, they feel fast even at lower speeds which makes them a lot of fun to ride. When they are on sale it is a great value.
Oregon winters are wet and chilly, and these boots make all the difference. I use them for road riding, with SPD pedals. They don't leak up through the cleats as some shoes do, and the shell is truly waterproof. I find them comfortable down to about 33 degrees, with thick socks. I've ridden in heavy rains for hours many times and they never leak... except, as with every winter shoe I've used, water can get in from the top, and the neoprene collar will soak up some water. But even after riding for several hours, this has not resulted in water leaking down into the shoe. If you're really hard-core about dryness, use gaiters to cover the upper shoe collar, and pull your rain pants down over the gaiters for a perfect seal. I do recommend getting the WIDE version, even for normal feet, as the "normal" fit version made my narrow feet feel pretty claustrophobic. Lastly, the soles are very good for walking, when you need to.
There is nothing in this world like a shift on a Shimano front setup. Even their old mechanical stuff worked like butter, but the Di2 setup is nuts. Shifts every time, quiet, smooth, can do it one-handed, it's the best.
The crankarms themselves I have no issues with, even with the recall going around. The rings are where the magic happens, and it's worth it to me to not think twice about a front shift, or grinding it out a bit more in the big ring just to avoid that dreaded potential drop from other setups.
Great crankset. Catch a sale and treat your bike.
For winter weather I strongly recommend winter shoes. I tend to have cold feet and these winter shoes make biking in mid 20'F temperatures much more tolerable. I wear wool socks and these shoes and can last for about 2 hours before taking a warmup break. I had tried regular shoes with shoe covers and chemical hand warmers, and these shoes are much warmer. I wear these in the same size as my summer Shimano shoes and find the fit, with moderately thick wool socks, to be good.