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When I change environment variables in WIndowsXP I have to restart before emerge detects them.
What environment variables are you trying to change?
You seem to have CSS turned off.
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You can test this using Gnumeric. If you set the User Variable LC_ALL to fr_FR it should change the menus to French immediately. Under eD you need to reboot.
The PATH is a big one. Installers often add to the PATH and then you have to log out and log in to see the changes. The earliest process that can handle windows messages needs to handle WM_SETTINGCHANGE. Specifically, the process then needs to read the registry from the path and update the PATH variable. New processes created after the change would then see the new PATH variable.
This isn't just a Windows XP problem--it is for every version of windows.