A friend of mine wants to do a road trip on Route 66 from Dallas to
Chicago. I'm thinking he's thinking the Route 66 of legend is just as
interesting along that stretch vs. going West through New Mexico,
Arizona, and California.

A colleague at work from New Mexico says Route 66 gets more
interesting the further West you go. I guess everyone has a different
idea of "interesting," but deserts, mountains, ghost towns, old mines,
etc, sound interesting to me.

1) Isn't the Route 66 people get nostalgic for, and where the most
interesting bits are, the stretch between New Mexico and California?

2) How advisable is it weather-wise to road trip from Dallas to
Chicago along Route 66 in January? Seems like he could run into some
nasty weather, especially since he may go even further north past
Chicago.

3) What is the stretch of Route 66 between Dallas and Chicago like? Is
it interesting and worth the trip in and of itself? Is it crowded and
dull? Empty and dull?

4) Is the Western part of Route 66 "too touristy?" (an objection my
friend made to doing that particular stretch) Or does it simply have
some kitsch every now and then stretched out along hundreds of miles?

5) What are some highlights of the portion of Route 66 going north
east to Chicago from Dallas?

I guess another objective of my friend is that he wants to ultimately,
some day, have driven through all 50 states--and he'd prob. pass
through a good number of states on his trip. He's also from a small
mountain town in North Carolina and wants to see more of small-town
America elsewhere in the country. He's also a photographer as part of
his day job, so my guess is that he's hoping to get some great shots
out there on the road.

Us both being from North Carolina, I personally think he'd have a
better time flying out to Dallas (purpose is to visit a friend there
first for New Years), renting a car, heading West of Route 66, then
flying back to NC. Seems like it would be a whole lot more
interesting. I wanted to go on the road trip, but couldn't justify
taking the vacation time to do the portion north / east of Dallas
without ever having done the Southwest portion.

Probably any day on a road trip anywhere is better than a day spent at
work. But as far as Road Trip A vs. Road Trip B on Route 66, which is
better and why?