Oregon Hikers

I decided to delete this post. Nothing to see here

My opinions on skiing MSH (YMMV):
Most people carry their conveyances on their backs because of the problems you experienced.
Ice is the one thing that can cause problems for skins on non steep slopes. Steeper icy slopes get you closer to that failure point.
The last half mile at the top always seems icier than below it so starting your run there will get you a good run and save you time. Obviously, you lose the view and some down route selections.
Oddly, many people ski close to the climbing route. There's so much more if you traverse away, left or right.
Try to follow a skin track up. Somebody did some hard work for you so enjoy it. Skinning on a foot path usually doesn't work well.
As always, get avalanche safety training and actively practice what you learn. Get properly equipped for safe travel. Accept that high risk can happen which will require you to alter your plan including turning back.

And Middle Sister is a long hike from Obsidian TH but it's straightforward. The pitch to the top from the middle/north col can get tricky due to weather exposure. Recent snowy weather might present winter-like difficulties. I would not try to ski it. There will be lotsa rox.