I would not consider this a "considered approach." He's doing a multi-year, ground-up rewrite of a highly successful product in order to add a list of features geared towards Textmate developers (of which there are roughly 1), rather than end-users.

Meanwhile, he gets so many complaints from dissatisfied users wanting a few core features added to the 1.x version they paid for, that every 6 months he writes plaintive blog posts telling people "I'll release it in another 6 months: software is hard!"

This is the portrait of a project that's being sadly mismanaged into irrelevance, not one that's being carefully honed to perfection.

What I find amazing is the sheer cognitive dissonance of Textmate's popularity in the Ruby community; the same community that has enthusiastically embraced Agile developer practices and whose leaders tend to speak as often about the importance of good project management as they do about good coding.