It seems to me that the author of TextMate is in a rather interesting position. he has created an editor with a cult like following that he has neither the time, manpower, or interest in updating. I am sure that version 2 will be completed at some point, but at what cost to his sanity? Imagine for a moment if he just gave up and released the source for free. Hundreds of itchy fingers across the net dig into the sourc…
Seriously though, I think the picture you paint would work out very well for him, but judging from bits and pieces I've read over the years, I suspect the Textmate code base is not particularly well structured and that he might even be a little embarrassed for others to see the code (I'm just guessing based on scraps, but I think most of us have been there).
It's clear he's made a few million euros from Textmate and I've read that he has a few pet projects he enjoys working on (for some reason I think I saw DHH say this). Perhaps he doesn't want that fame or the big bucks. I could certainly survive full time with a few million in capital and a residue of sales each month.. (even if he sells a mere 100 copies a month now, that nets far more than the median European salary).