Thanks everyone for the replies, and inspiration, if you will.
The more I read, the more it seems the stuff I'd have to worry about is stuff I've already taken care of. New in the past two years are the rear suspension (mounts, links, diff mounts, wheel carrier bearings), axle boots, all calipers, discs, hoses, rear brakes lines, shocks, front and rear wheel bearings, center link, steering damper, flex discs, center bearing, trans mount, radiator, coolant hoses and tires. When I makes that list I feel pretty confident. I think the thing that concerns me most is that it does leak oil (onto the engine's bottom, very rarely onto the ground), but it also make sense as a few of you have said that if this isn't a problem over the course of 1,000 miles of work commute, it wouldn't be after 1,000 on the highway. I don't hesitate to use it for everyday driving. I don't have to replace any oil between 3k changes, let alone 1k miles.
I do try to remind myself, and my dad (who really worries even more than I do), that a lot of road hazards can happen in any car an in any place, like RML said. Example: I sustained $6,400 of damage to my Jeep last winter when I hit a massive deer a mere 2 miles from my house.
Assuming everything goes well over the next two weeks, I think I'm gonna give it a try. I took an extra vacation day to give myself extra time to get up there. I used to approach road trips like they were the 24 Hours of LeMans but I think I'd rather enjoy the road anyway. My alma mater is on the way, and I'd like to marvel at Niagara Falls a bit too.
dropnosky, I think I like your mantra best: "Personally I prefer to do stupid road trips in untested vehicles"
I aspire someday to embrace this lifestyle.