That's a hell of a long trip. How long are you planning on spending on the road and over what months? I've never taken a road trip that extensive. I'm currently planning a 2 month trip out west alone (I'm 22), not quite as massive as yours, but even my trip seems like a lot. Maybe this isn't what you want to hear, but I would suggest not spreading your destinations out so much. You will be covering most of the U.S. and could probably cover over 25,000 miles as well a spending a sh*tload of money. I would like to see your tentative plans when you figure them out. Sounds like regardless of what you do, you'll be seeing some great sights.