I’ve read a lot of interesting posts/thoughts/criticisms of the Moveable Type licensing changes (Feedster search). I probably have a somewhat unique view on this as an indy developer and a contributor (though I haven’t contributed much lately) on a competing product: WordPress.
One complaint that I’ve seen repeatedly today from various people is that the announced licence tiers leave too big a gap, that “there isn’t a license for me.” I’ve never spoken to the folks at Six Apart, but I’m sure they thought long and hard about this and they probably have a reason for it. Perhaps they want to see these users move to TypePad. Perhaps the support for individual users takes too much time so they decided to price the licenses where they would not be as appealing to individuals.
I know that SnapperMail choose to take this route with their Palm e-mail software. From their Yahoo Group:
We had lots of price complaints at SnapperMail when it was $34.95 and $44.95. When we pushed it up to $40 and $50, the complaining stopped. We figure we hit on the right pricing for our target customer – the tech-savvy professional – whilst leaving behind the budget concious consumer which typically are the ones that let us know we charge to much.
Geof noted this about my Tasks pricing; Tasks Pro™ isn’t aimed at the individual user and the price reflects that.
Anyway there seem to be a bunch of people planning to move over to WordPress because of this, I hope WordPress is ready for it! In some ways, WordPress seems to succeed in spite of itself. The docs (though improving, thanks for the hard work WP doc writers!) have been historically inaccurate or non-existent. There are various people who (intentionally or not) give off a very negative vibe when 
helping 
I think it will be interesting to see how Six Apart, Moveable Type, TypePad and WordPress evolve as a result of these changes.