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Here is my situation. We have a new virtualized server that is going to be running either Win2k8 R2 server or Win2k11 server (we haven't decided if we will be purchasing a license for SBS or the standard Windows Server). It is going to be replacing our our current Win2k server that is our domain controller and DHCP server, among other things. Is it worth it to try to migrate settings from the old server to the new one on the same domain? Or would I be better off setting everything up from scratch, including creating a new forest?

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How many user, computer, group objects? –  Bret Fisher Mar 10 '11 at 20:43
    
It's a small business probably no more than 15-20 devices logged onto the network at once. –  Alexander Miles Mar 10 '11 at 20:45
    
"logged in at once" doesn't answer Bret's question. –  John Gardeniers Mar 10 '11 at 21:24
    
There are 15 computers/servers, 13 users, and I'm not sure what he means by group objects. –  Alexander Miles Mar 10 '11 at 21:43
    
Having just 13 users and 15 machines I definitely recommend starting from the scratch with a new forest/a clean environment. Despite of re-creating the user accounts and re-adding the machines, even if you need to rebuild your GPOs on the new system, you'll have saved time. But: "..amongst other things.." - I assume there is no Exchange server in that list? –  desasteralex Mar 11 '11 at 0:07
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its probably better in the very least to setup a new forest purely because of the newer features and security functionality given by the newer versions of active directory.

I would generally always recommend a fresh install from scratch as it helps clean out bumf and make you check if you really need that setting or if it is the most efficient way of doing something. often there are times where a new feature will eliminate some of the things you may have needed to do on the old server.

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I am going to just start a new forest from scratch. The new domain is the last thing I will implement on the server, as I will move DHCP functionality and whatnot to the new virtual server right off the bat. –  Alexander Miles Mar 14 '11 at 13:51
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SBS 2011 must be a new forest I believe. If you go Windows Server 2008 R2 then I would just dcpromo it, move FSMO roles, then dcpromo the 2000 box out of the domain. Lastly upgrade your forest/domain to 2008 R2 mode to get the new AD Features. You may have to leap frog through a temp Server 2003 virtual box if you can't get a 2008 R2 box to be a DC in a 2000 forest/domain.

Otherwise if you go from scratch the computers have to be removed and re-added to new domain, users get new passwords, groups are gone, and any apps you have like Exchange won't work. File/folder permissions have to be redone, etc. etc.

New and clean is nice, but not necessarily the fastest way. I've never seen a AD forest get "old" in a bad way. Nearly all forests built in the old days are still around so Microsoft does a great job of keeping it compatible and clean.

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I don't think I will need a temp 2k3 box, Microsoft has a guide for adding Server 2k8 or 2k8r2 to a 2000 domain. However, I need to upgrade AD to AD DS for this to work, and I am a bit worried that might do something to break our current domain functionality. I have never set up a DC before, or added one to an existing domain, so I am unfamiliar with the repercussions of updating the domain type on an older box. –  Alexander Miles Mar 10 '11 at 21:01
    
What your saying makes no sense, sorry. AD is the same as ADDS, ADDS is just the newer name for it in Win Server 2008 and newer. You may be able to add a Server 2008 R2 server to a domain running Windows 2000 AD, but you'll need to research if a 2000 AD can support a DC running 2008 R2. If you need help you can get someone to do this for a few hundred bucks on elance.com or ask a new question here at serverfault like "How can I quickly upgrade from a Win 2000 AD forest to a 2008 R2 forest?" –  Bret Fisher Mar 11 '11 at 1:45
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