Definitely keep an eye on the value, I don't know if you have carvana/vroom/autonation up there or anything comparable, but if you do check the value there regularly. My trade in value when I ordered in March was $30,000 (2017 longhorn) and I ended up selling it to autonation for $38,250 in May. I paid about $3,000 less for it 2 years prior to that and put about 35k miles on it. So it's definitely important to keep an eye on that, I took the gamble and sold prior to my new ordered truck being built and had to go truck less for a month but for nearly 10k it was certainly worth it. Of course having an extra vehicle to drive in the meantime is pretty helpful too, or if nothing else you can try to use other offers you get to increase your trade value from the dealer.