Does anyone know of either any systems or have house rules that model skill advancement via the Dreyfus model of skill acquisition?
You could argue that any skill system which has five (or so) levels could be mapped onto the Drefyus model. White Wolf's Storyteller has up to five dots for skills; Shadowrun 4 typically limits skills to 6. (Edit: in fact, I'm almost positive that one of the SR3 handbooks listed what one typically did at different skill levels in a Dreyfus-like way--but it was just flavor text.) They don't, however, limit what a character can do to the Dreyfus categories.
But you could also argue that you don't want to model advancement via the Dreyfus model given that it's somewhat contentious and not extremely well validated. For example, in Review of Educational Research v. 76 pp. 383-412 (2006), Unveiling Professional Development: A Critical Review of Stage Models by Gloria Dall’Alba and Jörgen Sandberg, we find that:
That is, you see lots of variation within a "level", to the point where it's somewhat questionable whether there even is a level. Therefore, it's not at all clear to me that Dreyfus has actually done any better than role-playing games at modeling advancement in an abstract way.