To answer your question more data is needed: Where in AK and BC will you be driving, i.e. how remote? Will you be taking side trips on trail or is it all highway? What is your tolerance for delays? What is your aptitude for performing repairs on the trail? What is your risk tolerance? Would you be more upset if you payed for an expensive tow and dealer repair or if you felt that you overspent on preventative maintenance?
Without that you'll get all kinds of opinions on what others would do that may or may not apply to your specific abilities, route of travel, or concerns.
That said, while I have very adequate mechanical ability I also have low tolerance for road problems and (typically) have little time to spare. So for me avoiding a breakdown is a big deal and I will always err on the side of doing a PM early than a repair later. In the case of your truck, however, I don't see much on your list that would concern me with only 75k on the vehicle. My primary concerns would be coolant (verify it's actually SLCC an not something the PO cheaped out on) and battery. It's likely that the batt is original if a 2014. If so I'd replace it. And do the oil change. It's a 4k trip and my OCI is 5k, so that's a no-brainer. I'd also bring a Noco jump pack. Brake pads can be inspected externally. If >5mm I wouldn't prioritize replacing before you roll.
My biggest concern for that trip would be to sustain life for several days should weather or an accident. Food, shelter, water, heat, protection. I'd approach if from the standpoint that the vehicle was a complete loss and burned and your bug out bag was all that you had. Hope for the best, prepare for the worst. I'm assuming you'll come down the Alcan. In that case you'd have help pass by at some regularity. But weather, crashes, landslides, floods, etc. create havoc and in the dead of winter can change an inconvenience into a harsh stay. Or worse. Spare fuel for delays, reroutes, back tracking, and idling would be premium.
Stay safe and post up pics of your trip!
