Networks

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

Wow! What a loaded question.

On the idea of Linux:
"We want Exchange, AD, IIS or Equivalent, Print, SQL". That's a lot of MS technology. I'd suggest sticking with Microsoft this round and slowly implementing Linux where it makes sense. It's too big a job to migrate all of that over to open source alternatives at once. Don't rush into it.

On to Microsoft:
I'm an SBS guy so can explain what you would get with SBS. The current version is SBS 2011. You'd want the premium version because of the requirement for SQL. Unlike 2003, with 2011 Premium you can install SQL on a different box (and they include a license for Server 2008 R2 Standard as part of the license so that you can do it). SBS still has a maximum of 75 users/devices, so you'd have to go device CALs to stay within that limit. As with 2003 the big advantage is a single CAL covers AD, Exchange and SQL and that CAL is cheaper than buying them separately.

If you knew for certain you weren't going to grow any bigger while you've got these servers then I'd say SBS is a great option. Keep AD and Exchange on the SBS box, SQL on a second, I'd buy at least one more box to add some redundancy to AD. For File sharing, print and IIS either use an existing box or boy more depending on load and budget. The problem is it's so hard to know what you'll be doing in 3-5 years. It would only take you to buy out a smallish competitor and it'd push you over the limit. The 75 users/devices is a hard limit so it's not one you want to hit. If you do happen to go this way I highly recommend purchasing a swing migration kit from sbsmigration.com.

I'd love to offer you some advice about going with separate Exchange, SQL etc but all my clients are on SBS. You may as well look up prices and make your own determination.

As to waiting for Server 8, unless there's something specific that is a killer feature for your company I wouldn't bother. I've only read a little but from what I've read there are some really nice features, but nothing worth holding out for.