Good OS for these specs..

2000 would run perfectly fine on that system... 256mb is more than enough to get it running smoothe. (I run a 300mhz with 384mb of ram, so trust me i know!)
 
I have Windows XP installed on my PII PC w/ 384MB RAM, it runs a little slow, it's faster than I though it would be.
Linux is only free if you download it, obviously he can't download it off the internet w/o a working PC. I checked to see the prices on some of the CDs they ship to you and it's like $30 or more for selected Linux OSes. I'm not sure about all of them though.

EDIT: my PII is 450MHz
 
yea some of our school micron peice of shits are 700 MHz and probably 256MB running 2000 pro so i'm sure that it'll do just fine, but if u do alot of multi-taskin like photoshop, dreamweaver, fireworks, and a few IE windows expect 2 wait a little lol, i do it alot of the school computers and the slow down a bit
 
windows xp lite! yeah! ... i would say windows 2000 also... but if not, windows xp wouln't be bad. i've seen xp on 300mhz with 192 mbs of ram..
 
i would go with ubuntu, thats what i have running on a very similar computer and it runs well... and ubuntu pwns to start with so....
 
lol, well ubuntu is great and all but he did say he wanted windows if possible, but i guess it's still good 2 mention thats a good os 2 i guess
 
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