So after speaking with T/C customer support they suggested that I start to gradually sand down the inside (breech) facing side of the extractor pin. I was assured that doing such "home-smithing" wouldn't void my warranty on the barrel so off I went.
I wrapped some 600 grit sandpaper around a piece of brass, maintained the 45 degree angle on the extractor pin and went to work. I went very slowly but was not able to remove enough metal to resolve the problem. After studying the pin design for a while I took a stone to the bottom side the pin along the entire length, taking maybe 1000th of an inch of metal off the bottom. Then I spend literally 20-30 minute with the sandpaper on the front of of the pin.
After all that work I put it all back together and now the brass comes out much more easily. I dug out a few different brands of brass out of my pile and for the most part they come out quite easily. The Samson brand that I was shooting last Saturday it still a little bit sticky, and requires a fingernail and a bit of force to remove but it no longer requires tools. The extractor pin still pulls the brass back out of the chamber, so no issues with it's "bite" at all.
When my action gets back from the smith (I'm getting a Bellm trigger job) I will see how it works in action. But it doesn't look like I will have to ship my barrel back to T/C which is great news.