I've tried a lot in the past as well, and after getting annoyed with proprietary OS X software (iBank in particular) back in 2009 or so, and not really liking GNUCash and KDEMoney (at least back in 2009) ended up writing my own open source simple app (native Cocoa, with a more recent Qt port for Linux) that I've been using every since on a daily basis.
In terms of the detail, I used to do very detailed breakdowns of categories, but now I don't really see the point: my app supports 'split transactions' (one of the reasons I actually made it, as existing solutions had poor support for them back in 2009), and I generally just use things like 'Food', 'Drinks', 'Essentials' as categories, as it never really made sense (at least for me) to detail them with such accuracy.
But for things like 'coffee', I do 'Drinks:Coffee', so I can see how much I am spending on fairly specific things, but I guess it's a balance in terms of whether it's worth the effort to record them so accurately compared to making use of the details.
Similarly, things like 'Car:Fuel', 'Car:Service', etc...