Greetings from a fellow Montreal lover (I assume you are one anyway), and a fellow real pilot (I’m just a student pilot at the moment).
I’m glad you downloaded LMN, and also glad you’re flying VFR. Cessna 208 is a good choice to enjoy MSFS in my opinion, though it’s a little too powerful (and thus easy) for the challenges I’ve taken on in my journeys. I recently flew across all of Alaska in a Cessna 172, with live weather in February. I did almost crash and die several times, but emphasis on “almost.” The 172 has no de-icing equipment so I had many close calls.
Flight planning when your plane is not a jet is a huge part of the fun of doing a trip like yours. I don’t think Newfoundland to Greenland will be too difficult in a C208. But what I am really curious about is how you eventually decide to cross the Pacific. This is the Pacific that killed Amelia Earhart of course, despite her plane having about 2,500 miles of fuel capacity. What will your strategy be? I am a frequent Pacific flyer and would suggest simply avoiding it: the landable islands are too far and few between. You may be better off sticking to Russia and crossing over into Alaska, which is easy in a 208.
Also, similar to you I do insist on two strict rules for myself: Live weather only, and live time only. In a C172, this means not flying on a particular day if the weather is atrociously bad. I still take risks a real-life pilot would not take, but I try my best to not ever crash in the simulation.
For another comparison of how to maintain a trip journal, here’s my current journey across India: