While I firmly believe fit is a personal thang, I found that once I wore my true size, things got a lot more comfortable.

I tend to wear all of my clothes a bit on the large side, so when I first started buying shorts, I just did what I usually do...buy something that really is a bit on the big side. Dumb! Chafe city! But when I bought the next size smaller, the problems disappeared.

Re: your hands, they often on fall asleep on me on long rides. I find it's more of a position rather than the amount of weight I put on them. I give then a shake every now and then. But then, my hands fall asleep pretty regularly because of--I'm guessing--where the nerves are in relation to how I lay my arms on things (chair arms, my bed if lying flat), so I've gotten to the point where I try not to let it bug me (mentally) anymore.