Calgary to LA, then North East USA

My friend and I are planning to come to the states in about a year or so and want to do a massive road trip (I guess that's why I'm on this site!) First off I'll say we're visiting friends in San Diego, Chicago and Calgary, (could they have been more inconveniently placed around the continent!) so that may explain if it's a bit of an odd combination. Now I don't have a lot of the finer details down perfectly just yet, just have a ball park idea floating around in my head.

The route I'd like to take is something like this: start in Calgary, Montana to Yellowstone and Wyoming, Salt Lake City, Lake Powell, Grand Canyon, Vegas, San Diego and LA. Not sure of the order from here but we'd fly to the East coast and do (in no particular order) Toronto/Niagara Falls, Boston, NY, Washington DC, and Chicago. Then fly back home to Australia. (Yes, another Aussie looking for direction in your country!)

So I guess my questions are:
1. On that rough route, have I left off any major sights along the way?
2. What's the best way to get around the North East area like I described?
3. What's the best way to get away from tourists. Hiking is high on our list of things to do.
4. We'd love to hire a camper van and just drive without much of an itinerary, but will this be a lot more expensive than just a regular car after you take into account accommodation costs and such?
5. Is it generally possible to pick up a vehicle in Calgary and drop off in LA? Or is there a better way to do this?

Thanks so much for any tips or general comments and help you can give. It's really appreciated :)

Welcome to the RTA Forum!

The biggest problem with your current plan is that typically you will not be able to rent a car in Calgary (or anywhere in Canada) and return it in LA. One way rentals across the borders are generally not allowed, in the rare cases where it can be done, there is a very high additional cost - on top of the one way fees you'll already be looking at. Your best bet would probably be to fly into Seattle, and then start the Roadtrip from there. You'd still be looking at a one way drop fee to return in LA, but they should only be a couple hundred dollars.

Similarly in the east, if you rent a car, you'll save money by doing a round trip, but as many of the metro areas are more easy to move around via pubilc transit, you'll have to decide how much time you are spending in each place before you can figure out what the best way to do your trip will be.

Campervans like you are used to in Australia just aren't very common in the US, and finding one as a rental is extremely difficult. Full sized RVs really have the market cornered, and in either case, they'll be quite a bit more expensive than just renting a car and staying in motels once you factor in all of the extra costs like camping fees, extra fuel, etc.