I started in 1E withthe blue and red boxes, and have happily switched over every time since then. For me, moving to the hardbacks was the smae game (I was very new then) and there was no angst. I was only playing with my brother at that time, and he had no angst either.
Going form 1E to 2E was much anticipated nad looked forward to, as I saw the changes in character detail and generation far more favorably. I was bored with vanilla rogue competing against vanilla rogue, and I wentto skills and pwoers for the same reason. Going to 3.0 was also \highly anticipated, as I was tired of 2E's restrictions and wanted mroe detail in t\my character. Some of the changes brought trouble, I will admit, but I enjoyed 3.0 and 3.5 quite a bit, though I too complained about the new 3.5. Luckily I have enough money to spend on stuff like this that it did not matter much.
But now, going to 4E it is the hardest change. I love 3.5's complexity and depth, and there is so much to do inteh ruleset, enough to do for years to come.
But I also like 4E, though I do nto dconsider it 1E-3.5E D&D, but a new branch off the tree. However, I can see 4E will expand greatly inteh future and become a better game, so I am looking forward to it. I will play both 3.5 and 4E for th forseeable future.