Okay, starting to pull a few things together:

-Primary stop #1 : Casper. Rest there a day, plus it'll give me an excuse to hang out there for a bit.
-Stop in Hiland before then for water/food
-Take at least 4 full bottles at the start. Getting from Hiland to Casper shouldn't be an issue, but I'm slightly worried over the stretch between there and Laramie.
-Looks like camping is going to be my only option after Casper.
-It probably won't be /too/ warm, but I'm leaning towards starting early in the morning, taking another break at mid-day, and continuing on after until early evening.