Why Exchange 5.5? Because not every small business feels they need to change what they're doing just because something isn't supported by Microsoft. (Just for the record, I have *never* called Microsoft for support of *any* of their products.) Because it still works and meets the needs of the business. With a SME server in front, intercepting SMTP attacks and processing the incoming stream for viruses and spam, Exchange 5.5 still works just fine. When there's a compelling reason to change, I'll advise my clients to do so. One will be changing out this year because they like Trend Micro server-based antivirus and Trend won't be supporting NT 4 past this year; one will be changing out next year as part of an assimilation by a larger company. Yet a third will be moving to Exchange 2007 in 2009 because we find we need to support a growing number of mobile email users and of course Exchange 5.5 isn't up to the task. (Many workarounds exist but they want the native functionality and the budget is in place for the specified timeframe.)
"If it ain't broke, don't fix it." Preventive maintenance, yes ... keeping an eye on the 16-gig maximum store size, yes ... replacing hard drives as needed, yes ... but change without a compelling business case ... no!