Well, as evidenced by the new provinces visited map on my signature, I made it to Canada and back. It was a great trip! While I don't pretend to know enough to do a real guide, I found that the process was very simple (just as everyone had said) and not a big deal at all. Here are some of the highlights.
You'll want to order your Canadian charts, which you can easily find from the standard sources. The IFR charts are updated regularly, but the VFR charts are only updated when there's a reason to. So if nothing changes (and there's not much to change up there), then they keep with the same chart. The IFR charts don't have all the airports on them (including some with instrument approaches). The charts do have a few minor differences vs. NACO charts, so it is a good idea to look over everything carefully and be familiar with them, especially if you're going into a busy airport on a bad weather day. I flew into Montreal (CYUL) and broke out on the ILS at 600 AGL, so it was pretty busy that day.
You'll also want to make sure you get your customs sticker. I got mine in 2 weeks from the time I ordered it, and that's pretty easy. There are a few other requirements that you should have, like a notarized letter authorizing use of the aircraft in Canada (assuming you're not the registered owner - in my case the plane is registered to an LLC that I own), a copy of your insurance policy showing that the plane is insured for flight in Canada, and some other papers I carried with me. I had them along just to make sure, but nobody asked for them.
Survival equipment requirements are interesting. If you're over "wilderness areas", you're required to carry survival equipment with a few exceptions. One of them is if you're in a multi-engine aircraft. I'd add the personal stipulation of a multi-engine aircraft that you know will be able to continue to an airport without your second engine. Where I flew, the terrain was low enough that this wasn't a problem in my plane, but depending on what you fly and your loading this may be something to consider. Keep in mind that your nearest airport may be more than 50 miles away. There's a whole lot of nothing out there, more than I've ever seen here.
The controllers in Quebec are bilingual and very good at it, they'll speak both French and English on the radio. I didn't hear them screw up once, they are sharp folks. They're also very friendly. The folks in Canada treated me very well all around, I was impressed and it made me want to return.
CANPass is a dream. Call up a few hours before coming, tell them what I'm doing, call them on the ground in Montreal and get told to enjoy my trip. No headaches, no hassles. You have to file with eAPIS both departing and returning to the USA, but this is not a big deal, although it's a bit more confusing than CANPass. CANPass needs to know when you arrive, but not when you leave, unlike the US.
Once you're in Canada, it's quite the experience. Get north of the controlled airspace and you're in the middle of nowhere. What's more, I was on an IFR flight plan and got told "Radar services terminated." After talking back and forth a bit I was able to keep talking to the controller for another 15 miles or so on flight following, and then had nobody to talk to at all until 70 nm south of Chibougamau. It's uncontrolled airspace. No separation services (there's nobody to separate you from), pick the altitude you want to fly at, and no controller to talk to. It's very different to anyone who's used to east coast American IFR flight. Got back on flight following about 70 nm south of Chibougamau, and then talked to the local radio when I got closer. Reported a bunch of things to them, then they closed my flight plan.
Speaking of flight plans, I filed my flight plans into and out of Canada on fltplan.com. I filed my Canadian flight plan with Canada's 1-866-WX-BRIEF, which was very friendly. They were very patient with me being an ignorant American. I ended up being a bit early, but my flight plan heading home apparently never popped up in the system. Quebec radio was happy to file a new flight plan for me (Quebec radio was different than the other radio I talked to for canceling and starting my flight plan). Next time I'll file my outbound Canadian flight plan with Canada.
I called Watertown, NY two hours ahead of schedule I was supposed to to let them know I would be there. I landed right on time, and they showed up 25 minutes late. It's hard to say what the exact problem was here. I was ahead of my eAPIS schedule by about 25 minutes (which I'd filed the day before, I didn't expect as quick of a turnaround as I had), so they may have followed that and ignored my phone call. So that meant I had to sit in my plane for 25 minutes while they drove to get to the airport. I think next time I'll try a different airport just to see if it goes faster. Anyway, they were pretty quick about their inspection. Walked around my plane with the radiation detector, and then asked me a few questions, looked at my passport, then said "Well, you're good with us." I hopped back in the plane and was on my way.
The whole process was very easy, certainly easier than I expected. While it does have a few extra steps vs. flight in America, those extra steps aren't very difficult. Canada is a beautiful place. It's a very different flying experience than America (at least the parts I've flown), but in a very cool, pioneering sort of way. I'd recommend it to anyone. I'll be making some more trips and am very much looking forward to it.
I've attached three pictures. One was Chibougamau airport where I landed (actually a very nice strip - next month where I'm going is "unimproved" and further north), one was a general view of all the lakes flying over that area, and then the last one is my GPS screen on 80 miles after taking off from Chibougamau. Lots and lots of nothing.