"Area" and "idea" are, I think, the shortest words to have the most syllables.
"Bimonthly" means two different things, and you can't always tell from context. On behalf of my language, I'm sorry. You'd think we'd have found a better solution by now. (As Douglas Adams pointed out before he died, "Do Re Mi" still has that awful filler line "La, a note to follow So...")
"Whine" and "whinge" have completely different origins but are one letter different and mean the same thing. (Huh; "whinge" is older.)
Woodchucks are physically incapable of chucking wood. BUT IMAGINE THE CHAOS IF THAT WEREN'T SO.
At least no word has more apostrophes than letters. Thank goodness we never have to write anything like z'hisz''''''''''''''''''''ott.
And also: every, EVERY, song with long "E" sounds in it, I keep wanting Bob Dylan to sing.