Thinking of moving to a Headphone system, thoughts

Ok, times are rough, money is tight. I love my system, but am kind tired of lugging it around with me...so far I have moved my system from Nebraska to Texas and then again to Michigan. I am now thinking of moving to a more urban setting such as Philadelphia or NYC...really, I would be happy to keep this system for ever, but need to start making "tough choices"

I was wondering if anyone else out there has done something similar? What type of products would I be looking at to keep the same type of listening experience? I think that I would probably keep my DAC and use it as part of my system, but I don't know...any input would help!

Thanks,