replacing 24 systems

I finally got a budget to replace 24 systems, (replacing old win98 celerons) These are new Dell systems. Is there a way to update and install the various programs to these systems on a mass level. Or do I have to set each one up individualy and do updates and patches. These systems are going to be installed at 2 locations. Both networks are on a workgroup. Also should I consider going to a serve at each location?