Marco has some good points in his Letter to Allan Odgaard, Author Of TextMate regarding his offer of TextMate 2 being a free upgrade to TextMate 1.
Given the value that we get out of TextMate, it's already grossly underpriced. Please let us give you more money.
While I prefer to side on the 'free' side of the fence, TM is a great editor and after 2+ years of work, I would have no issues with paying full price for a new version of the editor. Hell, I think you pay less for a full new version of your Mac OS every year (ish) ($30 vs $60).
Marco had other awesome stuff to say on this week's Build and Analyze.