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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.

even if you set up the cross check beach cruiser style it will still be a much fater bike....

maybe even a long haul trucker for added legth and stability if you want a cruiser???

i am thinking your never gonna be able to get your bars quite as high (relative to the seat) as that first trek though no matter what you do... you might be able to get close to the rivendell but oyu'd devinitely need a HIGH stem combined with some high bars.

I'd go with a MTB frame then. Add some slicks, some nice riser bars and a sprung Brooks. Plush crusin without looking like an old fart.

*Disclaimer: I got 6 grandkids so I'm allowed to toss around the term "old fart"

if you were to go with a bike for road riding, then you don't need front suspension - it makes the bike heavier and slower. I have a trek 7000 and chose it over other models because of the one-piece fork (since my commute is largely road riding

I vote cross check with bar swap. I think this will give you a "real" bike, with decent handling-yet still be comfortable. Hybrids are great for some, but I find they tend to ride like shopping carts. Besides, it's retro cool.