I punched out a roll pin on my 97 legacy outback and it seemed like it took more effort than it should have and when it finally came out it had been broken.
I went to put a new pin in and it was being a real bugger to work with so I took a look at the roll pin that had come out. It was permanently compressed.
Is it possible that the shaft from the transmission has a hole that is too small for standard subaru roll pins?
Here's a few pictures of the pin:
Here's the roll pin from the 97 legacy compared to a pin I pulled from a 99 forester last week.