I have used both chamois and gel shorts. For me, gel shorts work the best. They don't seem to wear out as quickly and they hold their shape better. I hand wash and air dry all of my bike shorts. It doesn't matter if it 10C/50F or 38C/100F outside I still prefer the gel shorts.

Saddles. You have to find the one that best suits you. Also, if you aren't a winter rider then each spring you will have to get your butt in shape just like your legs.