Re the question regarding a new road bike:

I don't know much about Trek at all. That said, since you mentioned that you are petite and have a short reach... have you thought of test riding a Bianchi Eros Donna? I think they run a bit pricier than Treks, but I have a friend who's 5'3" and loves her 46cm Eros Donna, and I'm 5'4" and I ride a 49cm Eros (the men's model) with switched-in girls' handlebars, and the reach is fine for me. I have heard that Bianchi is notorious for making bikes with shorter reaches (definitely shorter than, say, LeMond), and the Eros Donna is supposedly sized to fit not just a short reach, but a women's short reach. In fact, when I was testing out bikes, the reach of the 49cm Donna was just a little too short for me (but then, I've got long arms for my size).

Anyway, a 44cm would probably fit you, and Bianchi is ace when it comes to climbing hills.