re: upper back pain --

I had a lot of shoulder/upper back discomfort when I first started riding. I thought it was because I wasn't used to the position. After a couple months, i went back to the shop and got re-fitted. They had set me up fairly relaxed to start, but I wasn't comfortable, and I wanted a better position for racing. They flipped my stem down and lowered the bars (increasing my reach by quite a bit). The handling improved a lot, and no more upper back discomfort!

I don't really get any reach problems except in my lower back when my core is out of shape, or sometimes in my neck when my bars are too low such that it's difficult to look where I'm going. Maybe you need a longer reach than you thought! It doesn't really matter what it looks like to others--what matters is that you're comfortable! Your "functional" reach is more involved than your static body measurements. It has a lot to do with how you move on the bike.