I started playing D&D around 1990. I started with the Red Box that had come out most recently to that year.
Before long my fellow gamers and I got into 2nd Edition, and tried a little 1st Edition. Those were alright, but as I recall we didn't do much with them.
I bought quite a number of books, but wasn't playing with them enough to justify keeping them. I sold them all in about 1997 for credit at a game store. I bought a Star Wars RPG book (which I also didn't play much of but which had interesting books) and some cards.
In about 2002, I got into a brief play-by-post game that used the 3.5 rules. I like how things had been more codified and standardized and how a lot of the oddness and subsystems had been removed. Around the same time, I was also in a play-by-email game of Basic D&D with some old college friends.
I played 3.5 on and off for the next five or six years, with none of my games really getting off the ground. I was rapidly losing my respect for 3.5, because I was becoming more and more aware of the game's balance issues. It was a relief when 4th Edition came out and all the classes were balanced with one another. Every class could do cool things! Skill-based challenges finally had guidelines! Monsters didn't have to be made like players! I loved it, and I still do.
5th Edition just seems like a throwback. If it had come along, instead of 4th Edition, I might have appreciated it, but now it just seems like a throwback to 3.5.