I had a second today to work on the saw. I pulled the flywheel off and unfortunately the woodruff key looked fine. I was really hopeful that was the problem as it would be a simple fix. I'm still planning to pressure test it when I get time. Maybe the pressure test will show a bad impulse line or intake boot, but as noodlewalker said, I would have expected it to over rev if it was an air problem. I'm just hoping for something simple.
The confusing part for me, the last time I got it started I let it idle for at least 30 seconds. It sat on the ground idling fine, sounded perfect, I picked it up (still idling fine) but the instant I moved the trigger it died. It made no attempt to speed up from idle, it didn't spit and sputter, it didn't sound like it bogged down, it just sounded like I turned the switch off.