SlowToaddy is right but ...
OS 7.2.3 was pretty decent and then all after up to 8.6 (which was half way decent) then up to OSX 10.1 ... basically 3 steps that were good in between were very iffy ....
2000 and OSX cleared up a lot of problems for both companies.
I still love how XP and Office just decides to kill off Office for me
However, I still tend to think that Apple made the better user product. M$ is stuck with slap-dash companies producing oodles of software but ... end experience being that ... oodles of software. Apple and their authoritarian approach has helped to keep a pretty even experience, albiet marketing mishaps and what not in the past.
I tend to think that Jobso is NextStep and Apple

But, yes, NextStep was even a buy out by Jobso. Loved what he did to pixar though
Jobs is getting it pretty close to right this time around.
Ahhhh, enterprise ... run by the IT departments who are staffed by M$ people. The comfort zone can be good at times but you miss out on a lot of oppourtunities. Which is why I think the iPhone is the pandora's box for them.
SUN ... I keep watching them to see what they will do. They had the bull the horns so many times ... and like Jobso of the past ... seem to find a way to miss out on the big time adventures. Can they finally do it this time around? Problem is that I really don't what their focus is ???? In the early years I wanted a SUN workstation soooooo bad
MS being partnered with SUN is like sleeping with your ex
I like underdogs and I really hope that Apple and Sun will teach something to M$.