If you're really serious about longer distance riding, I'd recommend AGAINST cheaping out on gear. Generally speaking, you get what you pay for, and when you're in the middle of nowhere and you REALLY are counting on your gear, you'll be thankful that you got good quality stuff. Not to say that you have to go spending a bucket of money, but I've learned through about several hundred thousand kilometers, mostly on longer-distance road trips, that it's counter productive to be cheap.
Jackets - I don't like leather for touring, for the simple reason that if it gets wet, it's difficult to dry overnight. Few things suck less than having to put on a damp leather jacket first thing in the morning.
I have two jackets that are my go-tos. The first is a Joe Rocket Alter Ego, because it's very versatile. The "rain" liner isn't very useful for rain, as it's on the INSIDE, but it's a great windblock that's surprisingly effective at keeping me warm. And the outer layer of the jacket zips off for mesh. It sucks to be too hot. And it sucks to be too cold. And if you're out for any length of time, you're going to be both.
The second jacket is a suit - my Aerostich Roadcrafter one-piece. It's expensive, but worth every single penny. I went to the factory to have it customized, as my legs are very long, and while I was there I saw a rack of torn up, roadrashed suits that had obviously been crashed. When I asked about them, the folks at the factory shrugged and said that they had been sent back for repair after a crash. That, to me, is the ultimate testamonial - that folks crashed in them but loved them so much and had so much confidence in the company that they would send the suits back for repair rather than even buying a new one. Gore-Tex, as waterproof as you can get, easy-on, easy off. Lots of reviews of this setup if you Google it, so I won't go into a whole lot of detail except to say that after about 80,000 kms on my suit, it's well worn in but still in great functional shape and if I crashed in mine, I'd send it back for repairs too.
Note: Don't believe what anybody tells you. There's no such thing as water proof. Only varying degrees of water-resistance.
Boots - I've had a couple of sets of great boots, and again I'd never cheap out here - anyone who's poured water out of their boots at the end of the day, well, it sucks. Find comfortable boots with Gore-Tex lining or the like, that are comfortable enough to walk around off the bike in.
Shoes - Converse All-Stars. They pack small, so if you want a pair of shoes for just hanging out in, they're a good choice.
Underwear and socks: you'll discover in your first couple of road trips that it's not the weight that's the thing, it's the volume. Getting your gear to take up the least amount of volume is the trick. For me, underwear and socks take up a lot of room, and if I'm going away for 2 weeks, packing 14 pairs of socks isn't in the cards. I discovered Tilley underwear and socks, and I swear by them, although some people would cringe...they have travel underwear that's brilliant. Their advertising line is "two pairs of underwear to travel the world". Wash one pair at the end of the day in a motel sink, it'll be dry by the end of the night, rotate between the two pairs. I might not go to that extreme, but I've packed 4 pairs for 2 weeks and been fine.
Ditto with their socks - they're very comfortable, dry quick and don't stink. I can get 4 days out of a pair on the bike.
Packing - when you're first packing at home, don't ever pack to 100% of your luggage capacity. Pack to 80%. Because once you're on the road, you'll never ever get your crap stowed away as perfectly as you did that first time, so leave yourself some room.
Although I know plenty of people who don't agree with me, I think a good GPS is essential for travelling, simply because it allows you the freedom to get lost without having to worry about finding your way back.
Consider heated grips. And an electric vest. There comes a point in every traveller's journey when you need to keep moving, but you can't put on any more clothes, and for me, once my hands get cold past a certain point, I'm done - it's not safe to continue if my hands don't work.
Dunno what kind of bike you're getting, but consider hard, lockable luggage. It's piece of mind when you step away from the bike. And if you're in an interesting spot, and want to get a cool photo or go for a hike, being able to leave your bike without worrying about is worth it's weight in gold.
Invest in a good camera. Learn how to use it. Many of the places you'll go you may never go back to again, so take the opportunity to capture it. Take a little notebook, and keep track of the places you went to, the times you were there. Your grandkids, going through your photos on your lap at some point in the future wondering at how cool you were and wondering what happened to you since, will thank you for it. Buy a little tripod so you can get yourself in a couple of those pictures.
+1 on CAA - the money it'll save you on hotels / motels alone makes it worthwhile, and the free maps are great. For the first time this summer, I had to use CAA in the middle of the desert in Utah, and I'm glad I had it. It's cheap insurance.
Speaking of insurance, buy travel insurance if you're going to the states. One crash can be very, very expensive. CAA is good for this as well, but if you have other options, investigate them.
That's all I got for now.
I'm sure I can think of more.
