As far as the matching capabilities of Perl 6, I think they're trying to do something that will advance the state-of-the-art in terms of programming langauge integration in the same way that Perl 5's regex did. The Perl 6 rules are similar to the tricks and hacks that people do with regular expressions to build up full grammars. By separating out the parts into logical components, you will get better readability and reusability. Not only will we get cleaner text processing, but this (along with the VM architecture) will aid the development of DSLs that will extend the language into an exciting future.
Yeah, it's some good Kool-Aid and the Perl community been waiting for a while, but bringing these ideas into a production-ready language isn't trivial. I'm still using Perl 5 because of CPAN, but I feel that Perl 6 will eventually get to the same level especially with a source-to-source compiler. The hardest part would be dealing with native-code bindings.
Neat! I would say you should look into the NYC Resistor hackerspace, General Assembly, and the people behind different hack days like Music Hack Day and Photo Hack Day.
I don't know how many people you could get that would be interested in something like this since it probably doesn't have enough of a cool factor to draw people in. Maybe look at Code for America for some inspiration?
Heh, I'm not even from NY.
For GUI, I've had a great experience using Tkx. That is just a lightweight wrapper around the Tcl interpreter and there are nice tutorials for it at TkDocs.
For something to make bindings easier, there is work on a ctypes for Perl. And there's also the Inline namespace on CPAN, but that makes your code a bit difficult to distribute.
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