I can't give you any advice about the shorts problem becuase I love my biking shorts and am blessed to have never had any chaffing problems.

As for the jersey, you don't HAVE to get one because there are plenty of things out there that work, but they are definitely nice to have. I was initially hesitant to get one becuase I didn't want to try and "look like a professional biker" when I'm really not, however, when I finally did I loved it. The material is great for keeping moisture away from the body, they don't flap in the wind, and the pockets in back work great for my cell phone and GU gel. It was such a pain having to stop and get stuff out of my bag each time. Bento boxes are nice, but my cell wouldn't fit in it. Plus, you can buy one that fits your personality, anything from pretty bright pink flowery print, corona or miller lite beer print, or sponge bob square pants print. Good luck!!!

Hope this helps!
Roshelle from Milwaukee