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Server Upgrade - What path to go?

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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

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.