I found an article listing of 'Microsoft's biggest failures' via Doug off the Record's blog. Yeah yeah yeah... however it is the comment thread that really illustrate's the problems which have plagued that company. At some point you just have to be able to admit to a failure, here and there. Instead every legitimate criticism is vigorously defended against. Why bother?
Yet as I alluded to via a few different postings, in March, instead (IMHO) it's always the smaller things that always just bug me the most about Microsoft products and services. As a PC user, I couldn't begin to list every single thing made (or re-made) by Microsoft - that I would have chosen differently.