I'll echo some of the things the team here has said. Probably any transmission will work . . . UNTIL you start dumping the clutch and getting traction.
I'm old, and my setup is old, but, for the most part, we're both still running.
In 1994 I updated my '65 coupe with a 351W (409 stroker), a toploader, and a 9" rear. The Windsor is a solid lifter motor and, BACK IN THE DAY, was a hot little motor . . . around 500hp on the dyno. That was in '94, BUT that toploader is still doing fine, and she's a driver. That being said I fully admit she's no drag car, and I have a 3.00:1 rear.
I understand the heavy highway use, thing. I drove her mainly in Tennessee where it was 30 minutes to a decent place to eat. I just moved to Texas, and there will be more of that. The 3.50:1 rear is going to eat into the mileage for sure, but what you might want to look at is how much extra money is it going to be for the extra gas versus the extra transmission cost to get the OD. It may be one of those things where you'll save $200 in gas every year if you dump a few grand into a transmission. Meh?
If you go with the 4.11, though, yeah, you'll need to rethink that.
Just an old dude talking, but when you start getting into the 4.11, slicks, 500 ft-lbs, and I'm driving it to the drag strip on the highway normally . . . you'll either need a serious budget or truck with a trailer. For every guy who says "I've been running this setup for 2 years, and it's NEVER broken" there are probably three guys putting their car on a trailer because they can't drive it home. When you push like that with a limited budget, eh, you break things. And it's always that night when your friend with the truck is out of town.