You can assume anything hiked in the past week would have a relatively broken trail (although wind could drift it over in places).
Indian Pass isn't a winter destination, although you could conceivably do Marshall and/or Iroquois from Cold Brook, it would probably be spruce trap city for much of the way and take longer than another, more commonly used and broken out approach. So my point is -- if it isn't a peak bagging destination in the ADK high peaks, the odds of the trail being broken is very low.
There *might* be some skiing activity on that trail, but not sure how you would check into that since I'm unaware of any formal/thorough trip report page for ski conditions. There's a few facebook groups and websites that post more general ski conditions, nothing that specific unless someone involved with the page/site happen to do that trail and post something when you're looking for the info.
My partner and i broke trail for maybe 2-3 miles with skis and sleds two weeks ago coming in from upper works. We had equipment issues and turned around but that much has been covered at least. There was no sign of anyone having been in there before us. Enjoy