Number 1: comfortable riding weather does not equal comfortable sleeping weather. Worse - cool riding weather still makes you sweat, so after you've lost the activity-generated body heat, you're left with cold sweat to deal with.
Number 2: Never rely on wifi. This might seem like a no-brainer considering all the dead zones even within a place like Toronto, but in a city you're never really that far from access if you need it. This week I realized that you CAN be that far away when you REALLY need it. Should I be carryimg a physical map with me? Probably. Will I? Probably not. Paper takes up a surprising amount of space.
Number 3 - and most important: Have a plan, even if you don't need it. My days this week have always been easier when I had a specific destination and route versus the days when I figured I'd just ride until I got tired. So far, every day has ended differently than expected in some way, but it was always less of an issue when I had a fixed target to begin with.
So I've spent my day off planning my next week as best I can. I've set daily destinations - including alternatives, and contingency plans. Most important for next week - if I get lost, hwy 138 will eventually get me to Quebec City, and if the St. Lawrence is to my right, I'm heading in the right direction.