1e: I started playing SR when SR started. TBH though 1e was replaced by 2e in such short order, all I tend to remember are the wacky things that 2e fixed. Like, when using burst fire you used to make an entire attack roll for every bullet!
2e: Played this the longest and it's my sentimental favorite. Perhaps because it's my favorite, I don't think it has any flaws! Or because I haven't played it in about 20 years by this point, all I remember are the good parts

3e: I never really adopted 3e. I felt it fixed things in 2e that didn't need to be fixed.
4e: Where editions 2 and 3 were more or less newer iterations of 1st edition, 4e killed a lot of sacred cows. Limitations on the rule of 6? Dispensing with TNs? Is this even Shadowrun anymore? Yeah, I overreacted. But grognards gonna grognard. Plus 2005 coincided with a PCS for me, so at a new base I just fell into playing other games for a while with new gaming buddies.
20th Anniversary edition: missed out on it entirely during my Shadowrun hiatus.
5e: 2013, like 2005, coincided with a life change for me. In this case, retiring from the military and going back to school. Got back into Shadowrun just in time for 5e to be a thing. 5e definitely feels like a 4e MkII in the same way 2e was an organic evolution of 1e.The sacred cows that 4e killed have stayed dead, but so many people are used to that now they don't seem to miss them. In the grand scheme of editions, I'm not particularly a fan of 5e and really won't miss it once we move on to 6th world edition. I especially won't miss taking an hour to resolve a combat turn. But I have had a lot of fun with it, and if I were to pick a 2nd favorite edition this is probably it simply because I've played it so much over the past few years.
Anarachy: Never tried it, but am intrigued by the notion of a cooperative narrative style game in the Shadowrun universe. I wonder though how the setting is supposed to be oppressive and dystopian when the players are telling the GM what happens rather than the other way around

6th World Edition: It's shaping up to be a truly new edition rather than a successor edition in the way 4th was a break from 1-2-3e. Killing sacred cows has a way of turning people off. But I've been through that shock once already, and can absorb that kind of blow easier a 2nd time around

I'm excited for 6e. Particularly the streamlined rules... 5e does have a big problem in that arena.