Server upgrade from SBS2003 to Server 2008 or SBS2011?

One client needs to upgrade their sbs2003. Outgrowing the hardware and some newer OS would be great.

They are about 40 users (but 30 of them only use like Exchange Actiive Sync for email outside teh company) only about 10 use the fileserver, oulook, printing and applications on the server.

They may be about 60 users in a while but still only about 10-15 will be in-house the rest will mostly just use email remote.

They need server os, they need exchange. Buying client access licenses for SBS is soo expensive (like a 5 pack is $340+). The only reason I'm looking at Server2011 is thinking that they will save money on CALs and of course when having to PURCHASE exchange separately... lots of $$$.

Any suggestions on the best route OS wise for this kind of setup?
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Remember the limit of 75 users for sbs, sounds like you might be looking at playing close to this figure in the next few years and should be considering standard editions of server and exhcange.

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Cliff GaliherCommented:
Based on your current usage and projected growth (growing to 60), I think SBS 2011 Standard is a good fit. Businesses with a strong remote workforce are increasingly common that the RWA feature of SBS, combined with SharePoint and of course OWA, ActiveSync, and Outlook Anywhere makes SBS a solid choice for such an environment. I've deployed dozens for exactly these reasons and is a cost-effective way to help enable the mobile and remote worker be more connected to the organization.

kajbjoAuthor Commented:
Yeah but if 75 is MAX users that will become a problem in the next year or two...
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If SBS licensing is too $$, then perhaps they'd consider the MS cloud for email and files.. Office 365 has a cost effective entry point, and depending on how much storage they need for their files, it might even replace their file server.

There are some gating factors (no AD sync with the "P" plans, limit of 25GB email boxes, 25MB attachments, no Blackberry Enterprise services and more..) but many small business benefit from the no-hardware approach.  (You also get SharePoint, Lync, and Office Web Apps - big wins for clients that don't have the $$ to upgrade their hardware and software)

If you still need a local server (to manage the 10 users files, logons, printers, and apps, you could a) keep the SBS around with 10 licenses b) go Linux c) go NAS and scripts to automate logons and stuff.

Lee W, MVPTechnology and Business Process AdvisorCommented:
Why are you guessing about this?

Open Excel (or LibreOffice) and make two estimates - calculate costs and determine which is cheaper.  THEN, if SBS is more expensive, determine if the features of SBS are worth the extra (The price difference probably won't be much one way or the other).  

If you TRULY think you're likely to hit 75 users (not CONCURRENT users, but TOTAL users then you should probably NOT go with SBS - remember MS licensing is NOT for CONCURRENT users - it's for NAMED (not account names - but actual PEOPLE names) USERS and NAMED devices (consider named devices to be like MAC addresses - if you connect with it and it has a unique MAC address, it needs a CAL *IF* the user doesn't have one).
kajbjoAuthor Commented:
I ended up going with Server2008 standard w Exchange 2010. That way I can still use my old SBS2003 in the same domain for stuff if I want as well...
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