Yes, you can't loot the dead. And no, it won't look worser than any encounter. And isn't the travelling alone a "super annoying minigame", watching the small cross slowly crawling along the map?
In this case, grab a gun and walk, kill things. When you drive a car, you will at least have this imitation of driving. On the worldmap, while even in Tactics, driving was restricted to cities. And where do you want to drive, inmidst the mayhem of PvP or NCR Bazaar? Nope.
100% Death. Yes. Driving is dangerous, so you'll need a good driver and some people with guns to fend off the pests. A team. But hey, you're a faster and louder target in Wasteland and you have some more thrill.
And, what technical difficulties is a very interesting point. What problems would you expect? No, really. If you don't want it in 2238, no probs, maybe someone else want it.
I'm just interested in your point of view as a developer.
Would it be really easier to take the Tactics driving system, with all those collision data, multiple hex movement all over the map, animations and huge turning radii of vehicles? Not to forget the frames, unless you want 3d Hummers.
The advantage of my idea IS the "railroad trip", with the freedom on X and Y axis and you CAN escape but you can CHOOSE to fight.
So what if it looks like a minigame? So it's the minigame then, like mining, crafting or playing slaver. I suggested the most easy approach with most gaming freedom.