Hard tops typically go for about $1K in the WA/OR area so it might be worth your trouble to bring it and sell it here then buy a soft top. Just throwing out ideas, personally I really like having both but i Know it's not for everyone. I'm excited to follow your trip! definitely keep us in the loop. Lot of great suggestions in this thread.
I'd just suggest to take as much time as you can, doing cheap camping along the way if possible. Should be a really fun time, would definitely make for some sentimental value for the Jeep