Started with AD&D (1E) in the late 80s by reading the books, but didn't actually start playing until 1990. My brother's DM wouldn't let me play (he felt I was too young at 14), but changed his mind when I started making my own RPG based on what I had read of the books and CRPGs I had played. Instantly fell in love with it, and after a year, I started pestering my DM to teach me to DM. This turned out to be a good thing, because a year and a half later, he left the area, and I took over the campaign.
When 2E came available in our area, I and the group resisted it. We had all the 1E books (a gift from the previous DM), and felt that switching to a new edition was dumb. We continued with 1E for about another year, then I decided to pick up the 2E PHB. I found quite a bit of it was good, so I decided to mix and match 1E & 2E (which I found out later was VERY common). Eventually, most of the 1E stuff got phased out. Really hated late 2E though, because the DM option books were BAD and all the rules issues caused several groups I was in to fall apart.
Loved 3E when it first came out. Started to notice some problem by the time 3.5 was released, and was already upset about the half-edition change requiring new (more expensive) books, when most of the changes could have fit into a pamphlet (which someone eventually did). I never bought any books for 3.5, but at that point I was a player again, having met the best DM I know, so it didn't matter quite that much. By the end of 3.5, I again hated the system, because there were too many things I found fundamentally flawed with the system. Even Pathfinder's fixes (which were good), didn't change those fundamental flaws.
I jumped into 4E with eyes wide shut. I wanted to believe. I held on hope long after I should have known better. While it didn't have the fundamental flaws of 3E, it had it's own (more subtle) fundamental flaws that were ruining my fun. My favorite DM left the hobby over it, and I just couldn't bring myself to DM it. I continued to play mostly because that was the edition of choice for my current group, and I didn't want to stop RPing.
The announcement of the 5E playtest was heaven sent for me. Not only would there be a new edition, but I could help steer it towards the type of gaming *I* wanted. I worked heavily during the playtest, running Encounters, one-shots, and most importantly filling out the surveys (which often took 4+ hours). There were some aspects of the Playtest I was sad to see not make the final version, and others I felt needed to DIAF that made it in, but the basic framework of 5E is perfect. It can be tweaked and adapted, molded to become the perfect RPG vehicle for my game.
Of course, I always remember my optimism with 3E and 4E, and wonder if I'm once again filling myself up with false hope. Maybe by the end, I'll hate 5E and be ready for 6E, but I hope that's not for a long, long time.