I use DC's and I find them very comfortable. I do appreciate that the Bose sets are physically much lighter, and I am lead to believe, by someone I fly with regularly - he has not let me try them out yet so who knows??, that they perform very well at their job, probably the best around. It is a cost thing I spose, I guess that if you are after second hand then you are after saving money, which I think rules out the Bose.
I know what you mean about club sets, they never seem to fit, they always line up with my upper neck not my ears, not matter what you do with em, where do you get headsets that are that uncomfortable, it must be a flying club only shop!