Windows 2000 is probably the best choice for your laptop, but why not consider Windows xp since you have plenty of ram? Windows NT 4.0 doesn't support too many programs, especially in terms of games but I've never tried it. The only reason I could think of choosing 9x over W2K is the real time DOS, but drivers are likely to become an issue if you install a 9x operating system. I don't think your chipset even supports Windows 98 and without patches you can only use 1gb of ram, 512mb in Win95. Sadly Win9x lacks NTFS format, so you cannot have files over 4gb. TL; DR short summary of why Windows 2000 is a better choice -Drivers are avaliable (At least for your graphics card, not sure about the rest) -Can see all 4gb of ram -Two cores can be seen -More stable/reliable than 9x (Or at least that's what they say) -NTFS format which allows files to be more than 4gb -There are no drivers avaliable for Windows 95 -Windows NT 4.0 doesn't have many programs and is limited for games (At least I've read somewhere) Note: If you're going to attempt wireless internet connection (LAN) you're gonna be in for a nasty surprise. Windows 2000 lacks zero network configuration. Some computers/laptops will require a few more installations/updates for W2k in order for some drivers like Audio to work (Personal experience)