They almost had a viable solution for the SMB market
With the exception of boutique and creative business, such as advertising, Apple is mostly absent from the small business market. There is very little business case to be made for paying twice or even three times more for the same software and hardware (i.e. Microsoft Office + Quickbooks) to run a small business. Microsoft has always offered the best value proposition for small business and the use of PCs by most of them reflects that.
I work in the creative businessess, and my point is that even there Apple is losing it's place in the server room. For all it's faults, the Xserve was a solid piece of hardware and OS X Server was almost a fully functioning SMB server that had all the tools that a company needed, without any extra license fees. Also, the Xsan was a really, really cheap way of building a bonafide Stornext SAN, a mature storage system.
and a ease of use so far missing in other offerings
The two most commonly used software products in small business are Microsoft Office and Quickbooks. Whether these programs are used on a Mac or a PC makes little difference, so "ease of use" isn't a factor here.
I meant that the OS X server was easy to use, so that in many creative agencies it was run by an artist or a manager.
If they had offered a really good way of syncing iPhones to their Calendaring/Email system, something on par with Active Sync, it could have been a killer.
If it didn't sync with Microsoft Exchange, the most common choice in small business email servers, then it wouldn't add much value. If it did sync with Exchange then it wouldn't generate any additional Mac sales , people would just sync their iPhones with the Exchange Server or Outlook running on their PCs. Even if the syncing support had been better it wouldn't have been "killer". No small business owner would ever say, "You know, the Mac Calendering and Email syncing with iPhone works so well that I'm going to ditch the PC and the Exchange server and replace them with Macs!".
If they had had a way of syncing their own server system to the iPhone, I bet they would have sold a few more of the server systems. Nobody would have switched off a working system, but many owners who were switching to macs on the desktop would have taken a longer look at OS X Server. They didnt, so they decided to kill off the whole product.
They will try to enter the business market from the other end, with people learning to use Macs at home and users forcing IT-depts to integrate macs in their systems.
Which will never happen on a large scale. The IT department supports Macs and iPhone in the corporate infrastructure when C-Level executives or the people who sign the checks ask them to, but everyone else will continue to use the company issued PCs and standard desktop software installs and they will like it that way . If they disagree, they can find another job. Businesses care about making money, first and foremost. If being "cool" helps to make money then maybe, but for most businesses Apple offers less effective or at least no better business performance for a much higher price; that's a non-starter for official corporate IT support, especially in these economic times when IT support budgets have been cut to the bone.
I tend to believe that there in especially SMBs the Macs would offer a lower TCO, as they truly seem to need a bit less administration than their Windows counterparts (here I mean companies that do not employ full time internal IT staff). Otherwise I tend to agree with you. And "being cool because I use Apple" is such a useless straw man, I don't understand why you bother to throw it around.