Since having purchased my MacBook Pro last year, I have managed to successfully wean myself off of almost all Windows applications for my home life. The only Windows app I still use (and keep a Parallels VM for) is Microsoft Money. I am absolutely stunned that no one has figured out how to clone Microsoft Money on OSX.
I've probably tried about a dozen or so finance apps for OSX, but find each one lacking in some way. The primary deal breaker is that the majority of them do not offer automatic transaction downloading from my banking institution (Bank of America in Idaho).
If anyone has any suggestions, I'm up for them. The ones that I've already looked at: iBank, MoneyDance, MoneyWell, Money by Jumsoft, Cha-ching, iCash, and several other freebies.