Maintaining tasksel is annoying when I have to justify the choices it makes to other technical people who are annoyed at not having full control over this part of the installation process. It is conversely quite satisfying when I see actual users use it and be able to make choices at the level they're capable of working at, rather than just be faced with some unconfigured system that they're expected to turn into something useable on their own.
Aside from those annoying issues, these days it's a simple perl program written in a nice functional style, which has become quite extensible, so I'm pretty happy with that. I think it's the only program I've ever taken from C to perl; I tend to go the other way.
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