Soak the pins in Valvoline and use a big hammer to insert them. Just kidding.
I'd probably try to reduce the diameter of the pins rather than enlarging the holes simply because you can buy new pins but you forever alter the guitar. Call a machine shop and see if they have any suggestions.
Also, thanks a million for mentioning these. I've often wondered if they were a wise investment and it sounds like they are, but I'm also thinking is the sound improvement possibly due to putting new strings on too? Just curious.
"No Tele For you." - The Tele Nazi
Ha! Tele-ish now inbound.