Resale value is likely to be much higher with the Tesla due to the ability to do over the air upgrades to EAP and FSD. Degradation may not be as much of an issue in Canada as you mentioned. Adaptive cruise control will be an extra $5k as part of EAP, but regular cruise control is there, along with automatic emergency braking, and side collision alerts in the base model. You'll be paying an extra $5k to get the SL trim if you want adaptive cruise control on the Leaf, as I doubt it will be on the S or SV trims.
Another consideration, even if you do not need 220 miles range, over 10-15 years of usage, 15% degradation on a 220 mile range battery (187 remaining) is less impacting than a 15% degradation on a 160 mile battery (136mi remaining.) Although given a larger capacity, it will have less charge/discharge cycles making for less degradation. The warranties on both cars batteries are 8 years, 100,000 miles for the base (120,000 miles for long range Model 3.)
But going back to the first topic, any features you have on your Leaf are set in stone, while Enhanced Autopilot and Full Self Driving can be unlocked on the Model 3 whenever you like, (or whenever they work at a level that you're happy with.) Nissan doesn't seem to show any interest in allowing you to upgrade your Leaf in any way, as exampled by their refusal to put 30kWh packs into 24kWh cars when replacing packs. You must stay with the 24kWh. I'm sure the same will be with their ProPilot technology as well.
Just my thoughts, but in any event, from what I've read online, Canadians won't be able to get the Model 3 until late 2018 at the earliest, anyhow. My wait is until June 2018 for Arkansas.
Pulled the trigger on going EV on 10/2016 with a 2012 Leaf, and a Tesla Model 3 reservation expected to receive in June 2018.