Jobs was his own worst enemy for a while on the compatibility issue.
New OS launches- all your old programs don’t work on it.
Want to use a floppy to transfer files between a Dos/Win and a Mac? Nope, not compatible. When USB drives started coming out they dropped all support for floppy drives, even in machines with them installed.
Constant driver issues with all sorts of things. Many never got resolved. To be fair the market share for Mac’s was so tiny, offering support for them didn’t make business sense.
Want to play a game? Good luck. The majority of games didn’t work on Mac. Same reason as the drivers.
As for stability issues, for a while I ran a computer lab for a college 50:50 win/Mac machines. They both crashed about equally as often.