I'd lose the original skins, unless you're nostalgic. A little breathing goes a long way with the circumaural solution here. Only drawback I have found is it makes a power pig even more hungry.
Now for phase 2, I highly recommend trying out RPGWIZARDS dolby headphone config for Foobar. He (I think) has done excellent work with this scenario and it would seem almost tailored for the "flat" orthos.
Not really for nostalgia or anything, the donuts can wrap around the baffle but there's nothing holding it. The original pads help keep them in place with the extra material thickness i.e. friction.
The end result: angled drivers.
Also don't want my ears resting directly on the baffle.
Phase 2, I've tried it (or something similar) and I have mixed feelings about it sometimes. I do use it occasionally, without a doubt.