I was going to buy one my self , and although I haven't heard one (yet ) I've read as much as I could find about them. The He60 it self is a great headphone. One of the best , some people find it better then the omega II. The he60 is very fast and has great bass ,but it's detail isn't as good as the he90( but what is ?!). The baby orpheus which is the he60/hev70 headphone/amp setup is like on par with a srs-404/313 setup. The he60 is deff better then the sr-404 , but the 313 is much better then the hev70 , so over all there somewhat even. The hev70 is really the down fall of the combo so from what I hear the He60 on an amp like the KGSS is an amazing combo.
The k1000 on a good amp is much better then the srs-404/313( so I figure it would be better then the baby orpheus also), but the k1000 is prob going to cost you more then the baby orpheus because you have to buy a real powerful amp.
If money isn't to much of an issue I would recommend either the He60 ( alone) with the KGSS ( trust me that would stop your upgrading
) , Sr-404 with kgss ( sweet spot of the 3) , or K1000 on a good amp. Those are all around a simlar price range and all sound very good.
If those are all to high over your price range I would go with the he60/hev70 rather then a K1000 on a semi good amp, but maybe that's just me. The k1000 has bigger soundstage , but the he60 is very fast , great bass , great detail ( think the k1000 prob comes close with detail though ). Good luck