I've driven up and back to Alaska 3 times (6 border crossings) and had little to no trouble. In BC they want them to be cased and unloaded, in the Yukon, they didn't even have to be unloaded. They asked how many, what they were, and a couple times asked to see them, which I just opened the zipper cases, halfway, the guy looked and said "OK", then told me to have a nice trip. Can't take any hollow point ammo, even 22's, other than that, no big deal (I had a couple boxes of hollow point 22's, not knowing they were a no-no, they took them and gave me a reciept for them). I wouldn't want to drive all that way thru Canada and camp without a gun. The Canadian border people were always polite and business like, if not downright friendly, when I went thru. Stop on the US side before leaving and get a "registration of items taken abroad" statement that proves you owned the guns before leaving the US. That will help when coming back into the States. When I went thru, they just wrote the info on a letterhead note and gave it to me to take. They ran the numbers to be sure they weren't stolen, but that's all they did other than hand me the piece of paper to take along. Doing the current paperwork for the Canadians before you get there, should save time when you make the border.
I've heard a few stories about the border, tho I wonder if some people had attitudes when they went. I'm sure not all do, but, some americans seem to think that US law should hold sway in any country they go to. The Canadains don't see it that way. Respect their laws, and they seem to appreciate it was how I felt when I went thru, and in dicussing it with the Canadian border people. Get a snotty attitude, and things can get unpleasant very quickly. They can out-attitude anyone they come across. It's their job.
If you do ship handguns, you don't have to ship to or from a dealer (or pay that cost), you can ship them UPS (NOT by MAIL!!!!) from yourself, to yourself in care of someone up there, assuming you know someone, and the same coming back, BUT the law specifies that the receiving person that it's in care of CANNOT open the package. when I went thru Canadian customs, they asked if I OWNED any handguns, then asked where they were. I pulled out my shipping receipts and showed them, they were happy.
I don't think it's any big deal going into canada with guns. I've done it several times, and wouldnt consider going without taking guns.
I had all my pertinant papers in a folder under the seat, dog vaccinations, gun shipping receipts, US proof of insurance going to Canada, vehicle registration etc. I think 5-10 minutes was the average time to cross.