I don't see any dictionaries that list "aire" as a word (except as proper noun). I thought I had both "ere" and "err", but the former must have fallen off. Added it.
I'm not from Boston, have lived in many parts of the US, and everyone I know says "may-er". If you look for the pronunciation online, the examples I find are always two syllables in American English.
I like having they're. And I agree that in many parts of the country, mayor and prayer should be here- but then maybe so should layer. But not player. Isn't English awesome?
Yeah.. why isn't layer on here? The only one I can think of aside from that is Nair, which is a depilatory cream. but I guess it's a proper noun and probably doesn't count for that reason.
Just a thought on this... mayor and layer have literally the same phonetics on Merriam Webster. More commonly, they are both two-syllable words. Both have a one-syllable variant. If you have mayor as a possibility, you really should have layer. I would say layer in "brick layer" with two syllables, but I actually say layer in "two-layer cake" with one syllable, oddly. I've never heard mayor as having one syllable, but Merriam Webster says that it's common to say 'mer Johnson for Mayor Johnson.
How about adding “yeah” and “ne’er” (as in “ne’er do well”)?