Whilst it might install, Office Home edition will give you problems on 2008 - a retail licence only allows you to use a single copy, so why would you want to put it in a ts environment, even if it did work you would only have the licence for one dedicated client to access it.

Take a look at

http://download.microsoft.com/download/1/7/7/17745e4a-5d31-4de4-a416-07c646336d94/desktop_application_with_windows_server_terminal_services.docx

In brief the version installed on the server must be the same as the version licences on the desktop.

For what it’s worth, if you do install Office 2003 on Windows Server 2008 R2, the only issue I came across recently was DEP kicking in on Outlook.

I added an exception for Outlook, and scripted it like this in a .cmd file

@echo off

SET Outlook_Location="C:\Program Files (x86)\Microsoft Office\OFFICE11\OUTLOOK.EXE"

REG ADD "HKLM\SOFTWARE\Microsoft\Windows NT\CurrentVersion\AppCompatFlags\Layers" /v %Outlook_Location% /t REG_SZ /d DisableNXShowUI /f

If you want to script the automatic Outlook 2003 configuration via PRF file on first logon, then I used this script

@echo off

SET PRF_Location=\\company.local\NETLOGON\company.prf

reg query "HKLM\SOFTWARE\Microsoft\Windows NT\CurrentVersion\ProfileList" /v Default > %temp%\DefaultProfileList.txt

for /f "skip=2 tokens=3*" %%P in (%temp%\DefaultProfileList.txt) do set DefaultProfilePath=%%P\NTUSER.DAT

call set ExpandedDefaultProfilePath=%DefaultProfilePath%

REG LOAD HKU\TempDefaultUser %ExpandedDefaultProfilePath%

REG ADD HKU\TempDefaultUser\Software\Microsoft\Office\11.0\Outlook\Setup /v ImportPRF /t REG_SZ /d %PRF_Location% /f

REG UNLOAD HKU\TempDefaultUser

del /q %temp%\DefaultProfileList.txt

The other thing I came across at the same time was 123mrp.Net (if they use it) required running in 32bit mode with .Net Framework, which you can do with the corflags utility

@echo off

"%~dp0CorFlags.exe" "%ProgramFiles(x86)%\123mrp.NET\123mrp.NET Client\6.04.01.03\123mrp.NET.exe" /32BIT+