Newbie, have read entire post, have same problem.
Rylon, thanks for the qscript. I'm not clever enough to use it but it gives me a list of cures.
is the source but has not been revised since 2004.
"Algorithmic Shortcomings - One situation in which quotes will get curled the wrong way is when apostrophes are used at the start of leading contractions"
Matched pairs of quotes work fine for me but the above is a real problem when writing in an accent, ('ere luv a duck) or contractions of places ('Frisco) etc.
IMHO some of the answer would be for double quotes, single quotes, entities and apostrophes to be treated separately (on/off choice for each) unless anyone can revisit the daringfireball code.