Even if you had a bunch of analog stuff still going, my interpretation of your first post was that regardless of what may happen in the studio, you want to get the most out of your lap top on the road or just hanging somewhere else. What no one has mentioned yet is that the AKG K550 is not very amp fussy and, IMHO, does not get significantly better as you climb the ladder of DACs and Amps.
I think the DAC thing in general is mostly overblown beyond a certain point, and I think the AQ Dragonfly 1.2 is really really close to being at that point, meaning I think it pairs really well with the K550 and even though you may convince yourself that something like the ODAC or anything else in that range sounds ever so slightly better (and I doubt it really does...), once you factor in portability and convenience, the Dragonfly is a tremendous value... and looks cool and is fun to own, what's not to like? And after all that, I will throw this at you... you owe it to yourself to check out the Focal Spirit Pro, it is on my list as I recently sold off my K550, and I think it is the most appropriate headphone for your needs assuming it would have good fit/feel on your noggin. If not, I would still investigate the Sony MDR-7520 before sticking with the K550 longer term. For just home listening to jazz, folk, classical however, I would take the K550 all day long.