One of Microsoft’s key mistakes with Windows Vista was confusing customers with too many versions of the operating system (Ultimate, Home Premium, Home Basic, Business, Enterprise). Let’s hope Microsoft isn’t repeating that mistake with its newly announce Small Business Server 2008 offerings.

For starters, Microsoft is creating a new brand called the Windows Essential Server Solutions family. Lovely. So far, the two-person family includes Windows Small Business Server 2008 and Windows Essential Business Server 2008 for midsize companies. While Small Business Server 2008 is designed for companies with up to 50 employees, the Windows Essential Business Server 2008 is for “midsize organizations with up to 250 desktops.”

First, let’s give Microsoft some credit: With Small Business Server, the company has created a strong brand — and a loyal market following. SBS has hit a few bumps over the years because it wasn’t always easy for fast-growing customers to scale from SBS to full-blown Windows Server environments. But for the most part, Microsoft has dominated the small business server market by integrating multiple applications (SQL Server, Exchange, etc.) into a product bundle that partners could easily offer to their customers.

Now, for The VAR Guy’s concern: At a time when the world is asking for IT simplicity, Microsoft continues to roll out Windows brand after Windows brand. Microsoft says it did extensive research to help design, brand and roll out the Windows Essential Server Solutions family.

But The VAR Guy has to ask the obvious question: Was it absolutely necessary to draw an artificial line between businesses with 50 and few employees vs. businesses with up to 250 employees? The VAR Guy suspects this is another attempt by Microsoft to set aggressive prices in the small business sector, while charging customers slightly more in the midmarket.

Admittedly, our resident blogger could be wrong. And Microsoft has succeeded in the small business space where dozens of other server software companies have either struggled or failed.

Microsoft did not disclose pricing for Small Business Server 2008 and Windows Essential Business Server 2008 for midsize companies in its press announcements. Both products are expected to ship in “the second half of 2008,” according to the Microsoft release.