I appreciate the tip hiwall. When I had it apart, I took a .45 brush to the chamber. But was afraid to get too aggressive. I do think the chamber needs to be polished, but rather have it done by a pro. I'll post a follow up, and photo when I get it back.
I picked up my Winchester from the gunsmith on Friday. The issue was two fold. Lightly rusted chamber and the entire extractor assembly was missing. Apparently the rusty chamber made it hard to extract and the assembly gave out. $115 parts/labor and everything is tip top. Thanks for all the advice.