Lots of folks have skied there. There is an old hiking trail on East Osceola. It goes from the current Osceola Trail down to the Greeley Ponds. Shortly after it leaves the active trail it gets onto an East facing landslide scar which runs practically all the way to the ponds.
There are logging roads all through that area, although I hadn't thought any reached either of the Osceola summits.
"Moderate is not the new Low" - Chris Joosen, USFS Lead Snow Ranger.