Windows Server 2003 R2 upgrade

I have two servers one that acts as a file server and one that acts as a Terminal and Licensing Server supporting 40 clients both running Windows 2000 Server. What would you upgrade to Windows 2003 Server R2 or would you upgrade everything and why? This will be going to a Dell Power Edge 2900 with average specs. Could I safely put everything on this new server knowing how finicky Microsoft can be?
blueschaserAsked:
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Don S.Commented:
I would tend to upgrade the File server/Domain controller to 2003 R2 on the new box.  Mainly because of software support issues and it wouldn't cost all that much more.  Alternatively, you could just move your terminal server "as is" to the new box. Ohterwise, depending on how many users use TS, it could be quite costly to upgrade to 2003 on the TS box.  Either suggestion is really only a "temporary" measure as you will eventually need to upgrade both.
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iCoreKCCommented:
We have put W2K3 R2 on about 30 servers of every make and model, some over 5 years old, and have had no issues whatsoever.

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blueschaserAuthor Commented:
So your saying you use one server to host Terminal Server, Terminal Server Licensing and File Serving with no problems. I was told this was asking for it and wanted a reason why I should have one server for each.
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Don S.Commented:
From a licensing standopint, the Windows 2000 terminal server licenses are MUCH more flexible and geerous than the Windows 2003 terminal services licenses.  So, from that point of view, I would be tempted to delay upgrading the terminal server as long as possible.  I assume something else is acting as your domain controller?
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blueschaserAuthor Commented:
Yes, at this time the file server is acting as my domain controller. One of the problems being encountered is that clients accessing the terminal server are very slow and was told to upgrade now that I have a brand new server. I need to figure out what is best to do with it.
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ocon827679Commented:
Agree with dons6718 about W2K Terminal Services.  In W2K3 you need a client license for each connection regardless of the client OS.  In W2K Terminal Service, as long as you are running Windows 2000 Pro or XP you don't need a client license.  W2K3 causes a pause because of  potential budget constraints when dealing in a TS environment.
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