Townes Van Zandt Road Trip

Sounds like a great trip, all I could add would be to look to see if you could possibly try to catch a Steve Earl show as you make your way to Texas, he plays a lot around New Orleons and in and around Houston, who knows you might get lucky and you can certainly tell Townes and he spent a lot of time together.

Sounds like a fun adventure. I agree with tooblue in that you should listen to some Steve Earle along the way 

Perhaps unrelated, but as long as you're in Texas you can visit The Buddy Holly Museum in Lubbock. I'm sure Townes loved Buddy as much as the rest of us do!

Have you watched the great biopic about him (sorry, I’m blanking on the title)?   I’m sure you could get some ideas there.