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I think looks definitely count... And I think bike shop guys feel the same way. If not, then the highest end bikes would all be ugly instead of drop-dead gorgeous, right? Part of what has gotten me really into biking is the beauty of a really nice bicycle. Once I started paying attention to the style, it became just as important as the function. I think the car analogy is good... People who are into fancy cars, are really into the looks.
Definitely go for the clipless pedals right away. I bought a pair for my mountain bike years ago but was afraid I'd be trapped in them and crash, so I never put them on. :o When I bought my first road bike (Trek 1600) about a month ago I decided to go for it and had the LBS put them on my new road bike. I took a few rides around a large parking lot practicing getting in and out and I'm still kicking myself for waiting so long to try them - it is so easy you won't believe how quickly it becomes natural. Just find a safe place to practice for a little while.
I also second the idea of going with the LBS you feel most comfortable with, especially just getting into it like I am. There's a lot to be said for feeling welcome rather than a burden when you bring your bike in for an adjustment.
I debated mostly between the Giant OCR1W and the Trek 1600 (both close-outs so they were great deals) and went with the Trek mainly for the looks (along with the ultegra rear shifter over the 105 and it was a little lighter which justified the $150 difference in price). :)
Go clipless! Also, style-wise, you just can't rock a sweet ride like the Onix Dama without being clipped in! Taint right!
You can totally do it. If you want to practice clipping in and out - put your sweet baby on a trainer (LBS will have one you can use in the shop, or borrow one - you're gonna need one anyway if you live in the north) and get used to the technique.
Then ride on some grass and practice. It will take ten minutes to build the muscle memory to perform the task. If you fall, it won't hurt and you just might want to film it and put it up on youtube!
Also, any add ins, like arch supports, shims, that you use in your running shoes, put in your stylin' road shoes. My .02.
Go new bike!