Right now, I'm looking up times between places, odessa is 15 hours from LA, and tennessee is 15 hours from there, so we could, in theory, just drive to odessa the first day, sleep there, and hang out for part of the morning. I don't think driving from odessa to tennessee is a good idea to do in one day, so we'll have to look for a place to stop on the way.
Then, if I can get Sunday off, I should be able to drive to TN and either spend the night there or in Cincinnati, and make a leisurely drive home on Sunday.
Still a very rough sketch, but it looks like we'll probably be either getting into odessa very late to meet up early the next day, or we'll find someplace to stop between LA and odessa and then get into odessa early-mid the next day. Know any good breakfast places near there?
It's more what is along the route we are going on (or not more than XX minutes out of the way, whatever is in reason or deemed worthwhile to go out of way for in some special cases) that we can stop at and have a laugh during a rest from driving. That's mostly what I like it for. Though I did once use it to do an entire vacation more or less, nothing but going to see zany crap. Good times.
I plan to take frequent breaks (that are short if necessary) and your tool still sounds great for that.