Oh, many times! Flaming PB 5300s, the lost cause that was Copland, unstable 52xx/62xx models. No one has said that Apple has been a complete saint in this whole thing. The reason MS caught up was because Apple kept tripping up in the mid-90s. Once Steve Jobs came on, things started taking a turn for the better. And yes, MS did help out Apple, but only to look good in front of the DoJ. Without Apple, they would have been a monopoly and broken apart.
Remember they are a computer company like many others, and many others like Apple have had their fair share of bad decisions and bad hardware/software.
And for the record, Apple DID try to do what MS did, but without being sleazy as MS had been in gaining that 95% market share (the killing off of DR-DOS and other tactics to make MSDOS and Windows take the market). Remember that Apple did decide to license out the Mac OS to clone makers in the mid-90s, and it was great for consumers in the short term. However, from a business standpoint the clone makers were cannibalizing Apple's sales. Had that kept on going, Apple would be history now. As much as people think Apple should be a software compabny like MS, it is inevitably a hardware company. Of course, now that might change since their main focus now is the iPod and now they are switching CPUs.
Another thing about the Mac clone makers was that while their systems might have been cheaper, not all of them were very stable. Some Power Computing Mac clones and other Mac clones had huge stability problems that in a way was good for Apple since people knew that Apple's Macs were from Apple and would work without the instabilities of the clones.
So as much as I hate to say it (because I did love the clones), Steve's killing of the clones was good for Apple, and it definitely shows now. And now with a robust system like Mac OS X, a lot of businesses are considering the Mac for teh corporate space.
Here's some proof from not too long ago...
http://www.macworld.com/news/2005/07/21/osx/index.php