Earlier quoted context omitted.
In my household I'm the English nerd, although I have no degree behind it. I'd correct my wife when she wrote "would of" but then I listened closer when she talked: She wasn't saying "would've" she was saying "would of". That's when I gave up. There are a million other reasons to love my wife, and her proper use of 'would've' wasn't one of them to begin with :)
Does your wife actually pronounce these differently? Small sample size but as far as I can tell I pronounce these identically. (CA - native speaker)
She does not. They are the same to her. We're also native speakers from the Reno NV area, which is heavily influenced by Sacramento and San Francisco language.