I'm working with some of the guys on the maypole list to hammer out a new maypole roadmap.
Currently we're working through the outstanding issues and patches on the list and in rt.cpan.org to see which have been fixed/applied and what needs to be done for 2.10.
I think 2.10 will be almost exclusively bug fixes and a general spit and polish.
2.11 should be focussed on continued bug fixing, tests and looking at performance.
We aren't looking much further forward than that at the moment.
I personally have a few Maypole applications I need to update and develop. One project is implementing an improved bugzilla using Maypole, called Mayfly. Another is a super-secret project I can't talk about, the other is Pukka Plants Wholesale/Retail nursery which is a hybrid of custom modperl and maypole.
I think these as well as a re-invigorated project and community will inspire us for versions 2.x and what we'd like to achieve in the medium term.