Really nice idea. I never used V1 but looking at the screenshot I think the darker colours are nicer. If it's not too much trouble maybe you can add a Dark/Light Theme option, like arstechnica.com for example.
If a project is having a difficult time specifying requirements BDD can help to derive better scope. I have quite a lot of experience of BDD in small and large companies. And have found that it does help where stakeholder's are pretty vague about what they want, BDD can help them think about the User Stories in more detail. Which ultimately helps to deliver the right product. You can also do the automated testing part too so you have automated acceptance tests which become regression tests after the feature has been released. However, I also found that it's difficult to get all the people onboard with it as it takes more time.
TLDR; Good if you have problems defining requirements, difficult if you have uncommitted stakeholders.
We (my wife did all the visual/interaction design work) ended up getting to the point where the only thing blocking the initial release was the name. For what it's worth, "Toutday" is supposed to have a vaguely French feel.
Oh wow, don't know how I missed EpicWin... searched high and low before deciding to make it myself. Looks like an incredible app - I'll have to borrow an iPhone & try it out.
As far as deleting tasks they can't do - it's an honor system because you're only cheating yourself. It's like ticking ever day on Joe's Goals to pretend you have a habit streak, or entering broccoli for every meal in MyFitnessPal - defeats the purpose. However, let's say someone is level 10 with good weapons/armor, and they're struggling under a few goals. They could just delete those goals and recreate them for a clean slate. The downside here is that they lose all their historical data on those goals (it keeps a history graph of your progress), so there's some incentive to use Re-roll instead (or to just be accountable).
Now, once I get some 3rd-party productivity app integration (Pivotal Tracker, MyFitnessPal, RescueTime, etc) - those goals will be static (they can't edit them), and will be updated automatically. So that will lock them down a bit more. I'm planning on Pivotal & Pomodoro very soon.
I think this will be the solution I go with, but I'm a bit unsure how it would work in practice. I don't know how I would evaluate the accuracy of automated clustering?
Another solution might be a sort of automated-manual hybrid: e.g. identify common words/phrases in a particular category manually, write a script to find all items that have those, add to category.
Well to write the automatic bit you'll have to manually figure out the rules :)
But yeah, something like that would be a good start. I don't know anything about this domain so I'm of limited help here. It might be too hard to categorize based solely on words if they're not distinct enough.