I too definitely would have just gotten Jon 1.0 and spend the funds on upgrading him. Unfortunately, prices at the time were through the roof and I decided that wanting a Jon Snow in the collection, I would have to "settle" for version 2.0.
Fortunately, some time afterwards, I was able to grab the 1.0 outfit and gear loose. For a time there, I even put up Jon 2.0 and Tyrion 2.0 for sale but once I plopped that OSK noggin on it, it was a keeper. (and thus, so was Tyrion.)
Lord of the Rings is my main "fantasy" collection so I didn't want to dwell too deeply into GoT. That slope can be extremely slippery...
So in "trying" to control my GoT collection, I think that with these three (Jon 1.0, 2.0 and Tyrion 2.0) plus Davos and Tormund, I should be good to go. If I allow myself to slip down the slope, the only ones that I would consider adding would be a better done Daenerys and a well done Jorah...
Unfortunately, so many characters ended up being written disappointedly in the final season, that it dampened my enthusiasm for the line. Fortunately, that helps keep the figure additions under better control...
I did manage to get a great price on an Original Jon before I bought the 2.0, so that's now why I'm hesitant now. Like you, I never thought I'd be able to afford a v1. But the 2.0 is such a great looking figure I might still bite if I can get the 2.0 for a good deal.
GoT is definitely as huge world with tons of great characters. Its come so much later in my life that nostalgia has not even kicked in yet but I still have a much larger collection than I ever imagined I would. I'm tempted to get v1 Jaime because that early look is becoming hard to find, but prices are silly.
I enjoyed so many of the seasons before the last one that I kind of write it off like I do ROTJ or Last Crusade or Jaws 3D or Matrix 2/3 or Alien 4 or Terminator 3 or Pirates 3/4 or any Die Hard after the original or... well, you get the point.
Nothing ends well.