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I personally don't like Gore's chamois, but that's personal. Frankly. I think there are other options out there that will work just as well for far less money. Do you have everything else you'll need for winter riding? Hat, balaclava, windproof gloves, a good baselayer?
Winter riding is a crapshoot in Indiana. For several years, I was simply unable to get out from the first of January to the beginning of March. It's not just that it's cold: it's rainy or snowy and very windy. This past January, there were some cold (15 or so degree) but dry and sunny days that I was able to ride, albeit for short distances. I tend to think they're the exception, not the norm, however. So, that leaves November and December, where the weather on semi-decent days is near freezing or just a bit below.
I guess what I'm trying to say is be sure you're really into winter riding before dropping serious coin on tights. I like it a point myself, but after that point...I go to yoga or spinning.
Live with intention. Walk to the edge. Listen hard. Practice wellness. Play with abandon. Laugh. Choose with no regret. Continue to learn. Appreciate your friends. Do what you love. Live as if this is all there is.
--Mary Anne Radmacher