I think it's a pretty typical progression in just about any activity to get into it, buy some equipment, get MORE into and then realize the stuff you bought was all wrong. I know knitters who replaced all their needles after a couple of months and then bought all new yarn because they bought the wrong stuff the first time around.

I don't know if you can get uphill on a Pashley, but I'd like to be given the opportunity to try. Those are such pretty bikes. And I think I'll spend the rest of today drooling over the Lunar Cycles website. Gorgeous!

More seriously, we had a short discussion about upright/cruiser type bikes on hills that you can find here (also includes discussion about the Ticino): http://forums.teamestrogen.com/showthread.php?t=39594

I think any of the bikes you linked to would do fine for the type of riding you're talking about, but the Electra Ticino and the Therese have better (or at least MORE) gears that'll help with headwinds and hills. They'd also all be fine for riding with boots and shorter skirts, but if you're going to wear long flowy skirts, you'll want a skirt guard. The chain guard helps when you're wearing trousers (or you can just roll up the right leg or slap on an ankle band) or long flowy skirts.

Have fun shopping!

Sarah