I first used Windows in 1995 after not having used a computer since 1991 (Amiga WB1.3). I thought it was pretty good when I first started using it, but after a few days I started getting annoyed. It seemed that Windows was fighting me every step of the way. Things that should have been obvious were tedious and stupidly designed.
Then after being forced to use Windows every day at work, my annoyances became extreme stress. To cut down on the stress, I made a text file which I called "Windows Stupidity" listing all bugs and bad design that Microsoft never fixed. I added to it whenever I found a new bug or moronic design. That text file got pretty damn big! Anyway, when OSX came out I was thrilled. It blew away Windows! (at that time Windows NT/2000 - I haven't used XP)
Of course, then I decided to severely upgrade my Amiga and I'm happy and calm now. The Amiga is far from perfect, but I can almost always get it to do what I want - without it actively preventing me from doing things. Modern technology seems to be more about controlling the users and protecing investment, rather than ease and freedom of use.