Upgrade 2003 R2 Terminal Server to 2008 R2

I have a system with 3 physical servers.
     1. One is running Server 2008 R2 Standard with File Server, Print Server, AD, DHCP and DNS Roles
     2. The second is running Server 2008 R2 Standard with Exchange Server 2010
     3. The third is running Server 2003 R2 with File Server, Application Server and Terminal Server Roles (Main purpose is Terminal Server)

I would like to upgrade the Terminal Server machine to Windows 2008 R2
     1. Can I still purchase Server 2008 R2?
     2. Is there anything I need to be concerned about when upgrading the Terminal Server machine?
     3. I saw documentation about upgrading that talks about running adprep before upgrading. Is this necessary on a machine not running the AD Role?

The Terminal Server hardware is Dual Xeon 5148 Dual Core processors @ 2.33GHz and 4GB RAM
GreenWingRiderAsked:
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Will SzymkowskiSenior Solution ArchitectCommented:
Can I still purchase Server 2008 R2?
When you purchase your server license it will be for the most recent version 2012R2. You can then use that server license for 2008R2 (downgradeable).

Is there anything I need to be concerned about when upgrading the Terminal Server machine?
You will not be able to do an in-place upgrade you will need to spin up another server with 2008R2 on it. At this point you will need to re-create your licensing server and you will also be required to purchase your RDS CALs as well, because you are going to a new OS.

I saw documentation about upgrading that talks about running adprep before upgrading
Adprep is specifically for adding 2008 domian controllers to a 2003 DC environment. If you are only upgrade/migrating the 2008 Terminal Server then this ADPrep step is not required.

Will.
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GreenWingRiderAuthor Commented:
For my edification, why can I not do an in-place upgrade?
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Will SzymkowskiSenior Solution ArchitectCommented:
Is your 2003 Server 64bit? If it is not then you cannot do an in-place upgrade because 2008 R2 is only 64bit. 64 and 32 bit OS's are 2 completely different architectures so there is no upgrade path available. If your 2003 server is 64bit then it is supported by not recommended.

As stated, it is not a best practice to perform an in-place upgrade as you can have other underlying issues after the upgrade is completed. It is always better to do clean installations.

See link below for additional details.
https://technet.microsoft.com/en-us/library/ff972408(v=ws.10).aspx

Will.
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GreenWingRiderAuthor Commented:
Thank You.
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