Hey Guys - thanks for posting about this important issue! I think if you just ask Kurt and myself about bootlegs, then we understand that the recording and sharing of these, in 99% of the cases, comes purely from being enthusiastic about the music, which is of course very much appreciated! That kind of sharing is no different than what used to happen with cassette tapes back in the day when we grew up.
However, there are also other issues to consider. It is first of all illegal for us to sanction the illegal distribution of other peoples copyrighted material. Sorry for that legalistic phrase! So that means, in the case of the music from the Jazz Showcase, that all those songs that aren't Kurt's own (meaning all of them except "East Coast Love Affair"), we can't legally allow anybody to distribute those without the copyright holders of the songs being compensated.
Secondly, each venue, and indeed each musician who performs with Kurt, all have their own rules and level of enforcement of these rules to consider. At the Showcase, for instance, we had a fan who did not understand that it was annoying when he put his video camera right up in the faces (albeit from a distance) of the musicians performing - it is potentially very distracting for musicians who are trying to focus on the music and give the audience their all. The Showcase as well as the Village Vanguard, for instance, both have a strict no recording tolerated policy, and we ourselves need to adhere to this policy. That we feel is important as it can interfere with the gig itself.
All of this legal stuff is good and fine. The fact is that there will be bootlegs, and the other fact is that many artists understand that they should be happy that people want to listen to their music. So while they might not be able to actively encourage it on their websites, they might be able to turn a very blind eye to it when they know it's all in good faith. ;-)