Nice article!
I've been in the Netherlands since 2002, back then I would sometimes get up in the middle of the night to listen to the radio broadcast of a playoff game. The ones I remember were Leafs-Isles game 7 in 2002, Leafs-Sens games 6 and 7 2002 and Leafs-Sens game 7 in 2004. TSN would also have some grainy highlights on their website that I could watch the next day and then they didn't have any of the region restriction nonsense that they have now.
From 2006 my cable provider had the North American Sports Network which had the HNIC double header every Saturday (usually the Leafs for the early game) which I would tape and watch on Sunday. NASN became ESPN America which also had NHL coverage, but the channel was terminated altogether a few years ago, presumably due to lack of interest. Luckily by the time, the NHL online streaming services were available and that's what I've been using ever since. It works well, for some weekday games I get up before work and watch the game from the night before. I just have to avoid seeing the scores anywhere.