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Server Upgrade - What path to go?

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HAL 9000 Moderator

but we hope one day to rid our self's of paying so much for M$ licensing

and

If would need to run a active directory environment or emulate one, the client computers are all W7 Pro SP1,

Those requirements are at cross purposes however I would stick with the Server 2008 R2 as it pretty much just works does what you want and is something you are more or less familiar with though it does have a Command Line Interface if you want to use it. Though to be perfectly honest most people do things the hard way and use the GUI and end up with the worst of all worlds and something not performing as well as things should because they refuse to go to the Command Line for anything. Debian or any of the other Nix Distros on the other hand all have a GUI these days and even had then 4 years or so ago so unless you where using a very old version of Debian I'm not really sure what you are talking about saying that it was all CLI.

As far as reducing costs and using Active Directory you are stuck with Microsoft Products and the Weird Licensing that M$ sticks to to Gouge as much as possible from their customers. Though here depending on how many users and workstations you have the type of CAL that you use may generate some possible savings. If you have 78 users and only 50 workstations where some are being shared a Device CAL rather than a User CAL would be the better way to go .

Currently there are no costings for 2012 as it's still in Beta but I would imagine that it's going to cost about the same for the Server OS and CAL's as 2008 costs now.

As for Upgrade paths it may not be possible to upgrade from 2003 to 2012 so it may cost more to switch to the current Server Platform when 2012 becomes available and to be perfectly honest I'm not sure that there is a SMB to Full Server Upgrade Path form 2003 to 2008 but the Upgrade Paths supported by M$ are here

http://technet.microsoft .com/en-us/library/dd979563(v=ws.10).aspx

Just remember to remove the space from between the microsoft and the .com to get a working URL.

Currently all of my customers are still using Server 2003 so I'm not really Up On Server 2008 Upgrade Paths and while I feel that they need to move on their main applications need to be Rewritten or Certified as usable under 2008. That's the main sticking point no software available for the newer Server Platform yet and that also means that they are restricted to Windows Server Platforms for the foreseeable future at least.

Maybe some of the other TR Peers here will have a better answer for you but that's the best I can do currently.

Col