If pronunciation / language topics like this interest you, I stumbled across this enjoyable podcast some time ago: A Way With Words.
Listeners call in with questions and about 50% are about regional pronunciation differences (“Can you settle a bet on the right way to pronounce…”
The other 50% are on the origin of words or phrases.
I grew up in Ohio. When I went to college in Virginia, I noticed several of my fellow students would ask such questions as “Can I borrow an ink pen?” I wondered why the “ink” – it’s not like anyone would be carrying around a pen of the “pig enclosure” variety – until realizing that these classmates pronounced “pen” and “pin” much more similarly than I did, and thus felt the need to clarify what they sought.
And one I share. I’ve noticed that you can tell a native here by the way they pronounce their hometown: “Mi’waukee, WisGonsin”…
Sometimes even “Mi’waugee”, but never with an L…