It sounds like you still have a bit more research to do before making a decision, but that is probably half the fun in this hobby. 
My current setup uses my PC's optical out with CDs ripped to FLAC or 320 kbps MOG music subscription streams > a Nuforce LPS-1 linear power supply with the Icon HDP DAC/Amp > Denon AH-D5000s with J-Money lambskin ear pads (version 2)
I listen to all kinds of music across practically every genre, which is a big reason for me having to keep a music subscription service.
I did use a pair of HD-595s with the Icon HDP for a few months, without the linear power supply and using the computer's usb output rather than my current optical connection. Everything just felt a bit anemic, like chewing great-tasting food, but spitting it out rather than swallowing it. I was so turned-off by the experience that I vowed not to make my next headphone purchase a Sennheiser, after initially deciding on the HD-595s because my portable PX-100s were such an amazing value for the price and size. I even preferred the PX-100s over my Grado SR-80i's with my HeadRoom Total Airhead amp and Sansa Fuze mp3 player. After a lot of reading, I settled on the Denon D5000s that I now have, and I do enjoy them very much.
I have an Antec 900 computer case with the fans set at the medium speed, and my measured background noise is about 45 dB using a sound level meter; so I suspect that any headphone that isolates, even if only a little, has an advantage over a purely open set of cans in my listening environment. That said, in your situation, a different set of headphones would almost assuredly have a greater impact on your sound quality than anything an amp or DAC might be able to improve.
The Icon HDP is great little unit, but I really don't think it has the right amount of punch for my tastes. I'm actually looking to get the Burson HA-160 headphone amp and using my Icon HDP as the DAC and pre-amp. The specs that I can see indicate that the Burson is about 3-4 times as powerful. Because you need an option for your excellent studio monitors, it does not make a lot of sense for you to try and use a similar setup, that being an Icon HDP with an HA-160 amp. You will need the pre-amp RCA output for your powered speakers.
Might I suggest that you continue to use your Caiman as a DAC, since I believe it will provide a pre-amp output for your MC-15's while also supplying the source for a Burson HA-160 amp. The DAC will probably provide the least amount of measurable sonic improvement. You already have a good DAC. I say get the HD-650 cans along with the HA-160 headphone amp. The Burson DAC-only unit can be purchased later if the Caiman is just not doing it for you, but until then, you can grab a nice set of headphones that you can keep or sell later, along with a nice, versatile amp/DAC in the Caiman that you might find another use for, or perhaps sell it as well.
Edited by sonitus mirus - 5/17/11 at 8:24pm