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Ubuntu will definitely be the easier out of the two to install and use. As I understand it you can do a "Server Install" of Ubuntu which allows you to select packages individually, but I don't think you can use the GUI installer for that.
Both..
If your Hard drive is big enough why not ? then you can decide for yourself if you like the simplistic Ubuntu where more things have been automated and many choices have been made for you, or the more versatile but less automated Debian that has the largest package repos around but will make you work a little harder to configure some things. ..
Neither is a bad choice, One is pure Debian the other is based on Debian.
and since they both share the same package manager I can honestly say installing software after you have installed the system is quite simple.
I can't triple boot because my machine doesn't have a cd drive.
I will be using something called the ubuntu/debian windows installer. It installs directly from Windows 2000/XP, and you don't have to partition your harddrive (it somehow lets you dual boot without partitioning your drive, something about a loop?).
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