[Dr Q] How about "Day Moyn" for Des Moines, but "Noo Orleenz" for New Orleans (refer to Orleans, Normandy for original).

I thought it was pronounced Shrooze-brie, but it seems to be more variable than that. Near me is Caerphilly, pronouced Ku-philly, but then all the Welsh names starting Caer seem to be pronounced like that, eg Caerleon. It took me ages to get them right, and it's probably different in North Wales. I also remember a sea-side village in Fife, on the Forth, called Ainstruther, pronounced Ainster. It's really a plot to make fun of tourists!

Have a go at 'Mousehole' and 'Widemouth' if you would.

while we're at it 'Woolfardisworthy'.

renting a car in Dover from a place in the Maison Dieu Road, pronounced "Mason Doo" by the young woman working there. It's not just Americans...