I have 5 shorts, all different (hey! where did they all come from!), and the different types of padding don't really make much difference to me. I have one that's a favourite because of the padding, but they're all good enough, even though some are a bit sloppier than others, and one is really worn out. What does bug me on longer rides is the ones that have too tight elastic bottom hems. I like them on short training rides because they feel snug and "compressive" but they're irritating in the long run.
Bibs - I have 2 and am still not a total fan. I have had one bout of unexplicable stomach cramps on my road bike, which would have been better without two waist elastics (shorts+tights), but I've ridden many miles comfortably with just plain shorts. And it's a heckuva lot easier to go to the bathroom.
Winter riding is much less about badassery and much more about bundle-uppery. - malkin
1995 Kona Cinder Cone commuterFrankenbike/Selle Italia SLR Lady Gel Flow
2008 white Nakamura Summit Custom mtb/Terry Falcon X
2000 Schwinn Fastback Comp road bike/Specialized Jett