Looks like Haines or Skagway will be where we set forth on the long drive. Flip a coin? Is one route markedly better than the other?
I was going to add---Ketch
is the short haul. The trip up the panhandle will be amazing, though.
I personally like Haines better than Skagway. I feel like Haines relies on remaining relevant while Skagway relies on being historic, and I've come to find the whole gold rush, good time girls thing to be a little tired. I've never actually driven either route, only cruised into Skagway and flown into Haines, but the local highways are marked fine, same big green and white "next right/left" directional warnings as anywhere else; you're just not following Interstate shields. It takes work to get lost following main roads up here. There are only so many.
Prep-wise, your vehicle should be fine. I drove a T100 up half a lifetime ago. That was the last time I rallied around here in anything with fewer than 100,000 miles. I don't tend to be kind to them, either. Not listed, at 160k before a long or expectedly hard trip, I'd want to inspect my wheel bearings, steering gear, and the ujoints in the driveshaft, something you can do alongside brakes when you do them, and the chance is better than not they're still in perfectly serviceable shape.