Okay, so, update to put a bow on the actual move. It's been about two weeks since my arrival and it's the wee hours of the morning before my wedding. This is my experience as a Canadian using both UPS and Canada Post.
For sending things, I went with Canada Post primarily in terms of smaller shipments for five months leading up to the flight. I booked the flight early, got a really awesome deal, and called in my favors so I only had to pay about $60 to fill a tank to bring me to Calgary. Of course, I ensured nothing had hazardous goods (effectively, no batteries or the usual stuff you find on their site and that they state you can't bring before you even try to ship). At roughly 20 - 40 kg boxes they came out to about $150 CAD each. These made it as standard since nothing was truly "high value" and made it without a hitch. Maybe I was just lucky, but I'm taking the win.
Finally got to my expensive electronics. This time I went with UPS. I still ensured nothing was considered hazardous per requirements. For the sake of clarity and because I was cross-referencing multiple sources, I photocopied my K1 visa and main passport. For the manifest, I filled out CBP 3299 and provided this at the time of shipping. Per advice above, I went with general itemization but not being too general. Finally, I included my flight itinerary showing my date of arrival.
The only note, UPS charged me incorrectly, so I had to pay an extra $42.25 for delivery on top of the $300 for four boxes. Honestly not bad considering these were also in the same weight range. For those who prefer imperial, these were boxes weighing anywhere from 44 - 88 lbs. so by no means were they "light" by shipping standards. I was also very thorough with the padding to make sure everything remained well-packaged against breakage or the like.
Finally come flight time, I used precisely zero brain cells and filled up the carry on with all the battery-containing electronics and ultra-high-value electronics -- three laptops, my 3DS, my DSi, a wrist watch, my PS5, the stupid Wii U gamepad, just about everything but the kitchen sink -- and I ended up through security without a hitch. Didn't get stopped for additional looks at my electronics or additional questioning. In fact, customs was super nice. Was it worth the four days of muscle pain afterwards from bringing two weight-maxed carry-ons? Absolutely. Would I do this all again? Heck no. XD
In all, I spent about $1600 CAD on shipping my entire one-man household, $300 on my plane ticket, and $60 actually getting my ride to Calgary.