As far as I can tell, the only compelling reasons to get SBS are Exchange and Remote Web Workplace. Less interesting but useful features are Shared Fax and Backup. Most of the other "features" of SBS are free products like WSUS and WSS, or trialware (Forefront).
I'm playing with pricing here, and it looks like I can get Windows Server 2008 Standard x2 plus Exchange Server 2010 (or 2007) for only $1500 more than SBS 2008. (I only need Exchange CALs for a portion of the devices on the network)
I've running SBS since 4.0 and have always found it...annoying. For instance, I just read that in SBS 2008 we're limited to one network connection....which sounds fine unless you have a legitimate use for a second connection, like iSCSI, etc. Crap like this drives me up the wall.
So my question to you all is, what are the actual non-configuration-wizard features of SBS that I'm going to miss if I go with standalone Windows Server and Exchange products. So far I've got:
1) Remote web workplace 2) Shard Fax 3) SBS Backup (it's sorta neat, but I hear Server 2008 will incorporate it eventually?)
What else is unique to SBS that I'm overlooking here? Again, I'm only looking for usable features...not features that limit usability or supposedly make it easier to use.