Now that Microsoft has released VS 2010 I went to the product page here. To my amazement I found out that IntelliTrace(Historical Debugger) is supported only on the Ultimate Edition of VS 2010. This mean that you have to spend almost $4000 for renewal and almost $12000 for a new license. Does someone have any idea how can we change this decision? Especially make them add this feature to VS 2010 Professional Edition.
This is of course fundamentally a question to Product Management at Microsoft. They will have profiles of the intended market segments they're targetting. Willingness ot part with cash is one of those things, yes. But on the linked page, there's a small 2 line blurb that's also telling. The cheaper editions are expected to be used by individuals on small projects, the more expensive by teams on larger projects. Therefore many of the distinguishing features support those larger projects.
So, to answer the title question, you need to explain to MS Product Management that IntelliTrace is not a reason for you to choose VS 2010 Ultimate Edition, but it would be a reason for you to upgrade from 2005/2008 to VS 2010 Professional Edition. Since Vista, MS Product Management certainly understands version skipping, so this can be a convincing argument.