* When I'm trying to get an older operating system working in VirtualBox, and it decides that it doesn't want to work (is looking at Windows 95C... until I disabled PAE and AMD-V in the settings =P)
* Windows Genuine Disadvantage... need I say more? Some legit copies of XP, Vista or 7 end up being marked pirated while many pirated copies end up being marked genuine... seriously, Microsoft? This is just as bad as 98FE's Internet Exploiter integration (98SE at least toned it down somewhat, same with 2000/ME and beyond)...
* Sites that require Firefox or Internet Explorer... why can't I use Chrome? I'm sure it would render just fine in Chrome anyway... (in 2004, Firefox was shut out from sites that asked for IE... now Chrome, Opera and Safari are being locked out)
* Trying to find old drivers that are no longer available on many sites... hell, I had to find my 95C CD just to get my video drivers for my old S3 card when I reinstalled 98SE!
* When a program says that the operating system is not supported yet runs fine on Windows 7... a minor annoyance, but it's nagging me that it "won't run" when it actually works just fine (Songbird gave me that error, but I gave up Songbird because it kept messing with my MP3 tags and wouldn't work with my Sansa Fuze). =/
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Windows 98 forever!