I have a size 54 Ruby and the Tricross is a 52. It feels really good (and it might be the Ruby is a size too big for me). Neither have very aggressive positioning.

I think I like the handlebars of the Tricross better. The SRAM shifters are easier to reach and overall the handlebars just feel better when I am in the drops. When I use the drops on the ruby I can't really reach the shifters and brakes as easily.

I'll get the Tricross out for some real rides this weekend so I will let you know if there is a huge difference. (Also to compare road vibrations since the Tricross is aluminum.)

I bought the Tricross to be my workhorse. A go-almost-anywhere-and-get-dirty bike. It will also be my commuter (has the clearance for fenders and eyelets for front and back racks... the Ruby doesn't have the clearance, can't handle larger tires and no eyelets). So basically the Tricross will do what the Ruby can't.

I still love the Ruby though.