You only listed two road bikes (Cross check & Rivendell) and the other is a comfort hybrid (Trek 7300) and the last are town bikes (L300, Uptown 8).

I guess it depends on what kind of riding you intend to do. If you intend on riding more than 30 miles, the Cross check and Rivendell are the way to go. If you just like to bomb around town for 5 - 10 miles, either of the other hybrids will do just fine.

I would keep the Crosscheck with the drop handlebars and add inline brakes. This will give you the "upright" riding postion you want without scacrificing the extra hand positions. Oh... Don't forget to have them install a tripple.