Quote - Wait, how is that different from simply discounting the older version?

If I'm willing to stay one revision behind, then I pay $300 forever, and never pay the $1995 that funds the development of new features.

Isn't that how Caligari put themselves out of business?

The people that were paying the $1995 were the professionals who needed the new features to stay competitive, and they assumed these people wouldn't want to be a version behind.  Not sure what the upgrade pricing was on the Pro version, but it wasn't $1995 each time.  I'm pretty sure of that.

Caligari didn't put themselves out of business by doing that.  They let Microsoft buy them, gave the latest version of trueSpace away for free, and then were shut down by Microsoft when the economy tanked.  I think they should have sold it for something, instead of giving it away, but I also am surprised Microsoft didn't see a use for trueSpace in another department.  The XNA initiative could have made good use of it and maybe kept it going.  Then again maybe Microsoft didn't want to be seen as competing with Autodesk or blender by giving out a powerful 3D program for free.

There are features that it makes sense to charge pros an arm and a leg for.  Network rendering is a good one as most hobbyists do not have render farms at home.  64-bit makes less sense as nearly every new computer sold is now 64-bit, and that particular feature has already been implemented.