Win2k server or Pro?? with 98 and DEBIAN.. triple boot

[smp]

Okay.. currently I'm running a 98, 2000, Mandrake triple boot. I want to redo the whole thing. (I know, headache) I have been running win2k on FAT32 but recent breaches in my HOME network have led me be a paranoid android. I would also like to replace mandrake with Debian as that is the OS on my server, so I want to be able to compile stuff on this fast machine for the slower server. When I set up Mandrake, it made it pretty easy for me to make lilo my boot manager, I'm wondering if it will be as easy with Debian. I currently have a nice boot sequence going and I'de like to keep it nice. Also, I'm thinking of installing win2k advanced server because I figure that it can do everything that pro can do, and more. I would like to make a netbios server on it (to hold hands w/ samba on my debian box) and maybe some other networking fun. The only reason that I'm keeping 98 is cause I could never get win2k to work with goddamn All in Wonder to do capture. Please, give me some advice.. thanks.