Any OS has its strengths and weaknesses. IMHO, Amiga OS is for people (like me) who love the OS for its own sake. Many applications are showing their age, and the selection smaller but there are many ways to cope.
Other than being the same as 95% of computer users, it's hard for me to guess the attraction to Windows. Windows simply has more than critical mass, and is a magnet for viruses, spyware, and corporate control of the individual user. (I hate this!)
Classic Mac OS seems geared to creating documents, which it does very well. It's also more compatible with mainstream apps but seems to have fewer viruses and less corporate intrusion than Windows.
I'll stop pontificating now.
I ran OSX on a 300MHz G3, I found it to be annoyingly slow and combersome. OS9.2, however is sorta responsive, and when networked to my A3000, fills the several holes in my Amiga's abilities. If you go with OS9, find a copy of "Mac OS 9, the Missing Manual" by David Pogue. It explained most of the annoying questions I had as a newbie. Also there is a website that someone here gave me (can't find the link now) that lists all of the key combos to reset, clear pram, etc. These key combos should be in every manual, but Apple seems reluctant to pass them out. Let me know if you need them.