Migrating a WSUS server to a newer OS with many downstream servers

So here is my situation at my company. Our primary, upstream WSUS server is running Server 2003. It has about 20 downstream WSUS servers, running various versions of Microsoft Server (2003, 2008, 2008 R2 and 2012). 
My 1st question:
Is it fine to have the upstream WSUS server OS newer than the downstream WSUS server? I've heard a downstream server's OS doesnt matter, but I wasn't sure about the upstream server. 
2nd question:
No matter the answer to question 1, this server will need to be upgraded before July 2015. Can anyone tell me the best way to migrate an upstream WSUS server to a new server? Luckily it's a VM, so it will be fairly to easy to try and rollback if necessary,
but I want to see if anybody else has tried it. We also have about 15 computer groups that I want to keep. 
Thanks, Kyle 

My 1st question:
Is it fine to have the upstream WSUS server OS newer than the downstream WSUS server?
The upstream server OS should be newer than the downstream server OS. In fact, strictly speaking, an upstream WSUS v3.2 server with a downstream WSUS v6.x server is an unsupported configuration, although it WILL work just fine provided that KB2734608
is installed on the WSUS v3.2 server.
I've heard a downstream server's OS doesnt matter
It doesn't, if all WSUS servers are running v3.2 and at the same patch level.
2nd question:
No matter the answer to question 1, this server will need to be upgraded before July 2015. Can anyone tell me the best way to migrate an upstream WSUS server to a new server?
Yes, the *best* way to do that, which is discussed in this forum at least a few dozen times over the past several years, is to install a NEW server as a replica of the existing upstream server and replicate the upstream server to the new server. Then, reconfigure
the new server as the upstream server, verify the Product Category and Update Classifications selections are correct, and sync with Microsoft. Once you've confirmed the new server is functioning correctly, point the clients and downstream servers to it. Once
all downstream servers and clients have successfully connected to the new server, retire the old one.
I want to see if anybody else has tried it.
Only a few thousand over the past half-dozen years. :-)
We also have about 15 computer groups that I want to keep.
The computer groups will be automatically replicated (just like they are with any other replica server). If you're using Client-Side Targeting, the clients will automatically rejoin in their assigned groups. If you're using Server-Side Targeting, they'll
rejoin in "Unassigned Computers" and you'll have to reassign them. If you have too many computers to manually reassign (one would then ask why you're not using Client-Side Targeting), there's a
free tool at PatchZone.org that will export/import the client computers from the original upstream server to the new upstream server.
Lawrence Garvin, M.S., MCSA, MCITP:EA, MCDBA
SolarWinds Head Geek
Microsoft MVP - Software Packaging, Deployment & Servicing (2005-2014)
My MVP Profile: http://mvp.microsoft.com/en-us/mvp/Lawrence%20R%20Garvin-32101
http://www.solarwinds.com/gotmicrosoft
The views expressed on this post are mine and do not necessarily reflect the views of SolarWinds.

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    I do not have a document available for you, but I would do it like this:
    Make sure you have the same Word Version installed on both PCs
    Make sure the word settings are the same (Trusted Locations / Macro Security etc.)
    Make sure you have the same printers/printer drivers and default printer definied on both PCs
    Copy WWI and Expert Folder from one PC to the other to the same location
    Make sure you have the same PATH Variables defined on both PCs
    Makre sure DCOM settings are the same of MS Word and Adobe
    If you send PDFs make sure Adobe Reader and the tool you use to create PDFs is installed on both PCs the exact same way
    SetUp the Windows Services for EH&S Management Server, WWI and Expert on the new server exactly the way they have been on the old server.
    If your new PC has a different OS or newer Office Version I would do a complete new installation via the EH&S Management Server / CGSADM. Make sure to copy your Rules files and Graphics from the old PC to the new PC.
    Hope this helps
    Mark

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