Ha .. this is a better one over a beer or glass of wine ... or a few.
Warning ... blunt, male advice:
One bit of practical, though nerdy advice ... pay attention to her family, and her mom. This will give you some clue to the future ... it can also miss the mark entirely, but heredity tends to matter. Many women tend to look, and act like their moms, as they age ... just like us guys do with our dads (my laugh now sounds like my Dad's ... eerie).
And you sound like a guy who will avoid the "trophy wife" syndrome. Knockouts and wild ladies are fun to date (sometimes), but in my experience they aren't the quality package you're looking for. For me, I wanted a woman who was loving, intelligent, smart (not the same thing ...), good sense of humor (another intelligence indicator ...), sensitive, beautiful, sensuous and a good mom / caregiver. I ended up with a woman much better than I deserve, who became my lover, partner, mother to my children, and caregiver to our relatives.
But, she is my second wife. My first was a fine woman, but it didn't work. As the joke goes above, try to start with your final, best choice ... but you just have to take your best shot, and follow your heart and your head as best you can.
Sometimes trusted friends and relatives can (and probably will) give you their advice and comments as well. This isn't a committee decision, but if all advice is thumbs down, while you're charging ahead ... you may be thinking with the wrong part of your anatomy.
saluki9, interesting you mention the "friends first" situation ... same for me. In my case, when I met my wife she was actually married to another guy. She got divorced, I got divorced, and we eventually married ... no funny stuff ... neither divorce had anything to do with our friendship. As a matter of fact, we lost touch with each other over those years. [I still thought she was a babe when she was married though ... just kept a respectable distance.
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OK, one last edit, though I really, really hate to put this in ... prenuptial agreement. Since you're here, you may already be accumulating assets. For me, I was just about stone broke when we married. But I've seen some very sad situations, that could have been avoided with a well drafted prenup ... and believe me, these were very sad, life changing (damn near destroying) situations ... in one, a woman took great advantage of a man and his son from a previous marriage. A good attorney can be worth their weight in gold in such a situation. I cannot begin to give you advice on how to deliver this to the bride ...
This isn't a dress rehearsal ... it's life. Just give it your best shot, and enjoy.
Best of luck.