It also has nothing to do with the amount.
Next to the 'buy' button in 2005 there was text along the lines of "upgrades are free all the way to 2.0". Changing that now, added to the fact that we were all expecting much needed updates in 2008, is just a dick move. It (further) damages any confidence the community had in TextMate.
The fact that I would gladly pay $200 for my dream editor (even though I've already paid for TM1 and ST2, I'm lucky that this would be a practical purchase for me) is just not relevant. As you say, he is running a business. A business that made a promise about what buying the product would get you. End of story.
If I buy a car that has a big sign: "FREE WINTER TIRES", and 6 years later I'm still not seeing those friggen tires, does the fact that I can afford to just buy them make the dealership any less shady?