Very interesting question, and tough. The way I thought about it, is there any bike in production right now that'll you'll be able to say in 20 years "2010 _________ in red and black" and bike people will all nod their heads and be able to picture it?

My criteria for this:
1. brand/model reputation for excellence, maybe some race winning pedigree
2. distinct design elements
3. consistency of those elements over several years

The problem with most modern bikes in this question is that they change their design so dramatically from year to year.

My nominees:

Cervelo soloist (now called S1, S2, S3, one being alu, two and three being carbon)



This bike is from 2006, but you can look at their 2010 frames, and they look very similar.

On the Super high end, the Pinarello Prince:



You guys will probably scoff, but people go absolutely crazy for that bike.


For your second question, a good all weather bike, a few years ago they stopped painting them this way, but they use to offer the cervelo soloist team in a grey anodized finish, it looked great, really resistant to chips and scratches, and they pop up on ebay from time to time for very reasonable prices. Here's a pic: