I've been through more edition changes for various games now than I care to remember!
Warhammer is a bit of a strange one because each previous edition has got pros and cons and I play different editions at different times now. I play 3rd for its detail and oldschool-fantasy feel, 5th edition for heroic characters and 6th/7th for rank and file and 'balance'. In that sense, they might as well be entirely different games for which I can use largely the same army with the bonus that, because they are not played competitively, I can do whatever I like to chop and change the rules or add new units as I see fit.
Warhammer 40,000 went from very detailed (in 1st and 2nd) to gradually less so as time wore on. Mostly I just drifted away from the game although still have a fair collection and the occasional pang of nostalgia. If I went back now then I'd be torn between playing 1st/2nd or whatever the current edition is.
Mostly though, Necromunda scratches the 40k itch for me - even for that I am mostly playing the fan-edit of the 1st edition rules instead of moving to the more recent versions.
I started Dungeons and Dragons with AD&D 2nd edition, before moving to the more user-friendly 3.5 and eventually Pathfinder which is a third-party overhaul for 3.5. We never moved to 4th or 5th, but now have the conundrum of whether to pick up Pathfinder 2nd edition!
In terms of other RPGs, we played lots of 'old' World of Darkness and never got into the newer stuff, but might now be buying into 5th edition which is revisiting its roots.
So, I guess what I am trying to say is that each edition change has its pros and cons, some will be remembered fondly, others not so much and it probably depends on what you grew up with to some extent. In many ways I'm glad that many different editions exist for some of these games as it allows me and the group I play with to pick and choose which we prefer to use and which best suits our view of how the games 'should be played'.
What will happen with X-wing 2.0? I'm not sure. I might end up partially staying with 1.0 with certain players and move to 2.0 with others but I'm happy to wait and see how the game develops.
I can imagine that this is a far more contentious issue for players who are inclined towards pick-up games or those who play competitively and therefore find it important that everyone is on the same page.