First I would make sure your BIOS does not halt on errors such as Keyboard missing (This is setup by default but just a reminder in case you changed any BIOS settings)
Second I would enable Autlogon for Win2k:
1. Load REGEDT32.EXE from the WINNT\SYSTEM32 directory,
2. Ensure that the following registry String (REG_SZ) value exists:
Value data: "1" enables the NT AutoAdminLogon
Value data: The NT NetBios of the local machine or the domain name. This controls where the AutoAdminLogon attempts to look up the DefaultUserName (local machine or domain).
Value data: The NT Default User Name. This name must exist in the DefaultDomainName SAM database and have the DefaultPassword.
Third I would setup MMC on your regular workstation to manage any settings on the file server.
Fourth I would load Netmeeting and enable Remote Control option so that you can basically run the box from any other workstation on your network w/o having a monitor on the file server.