Stack Overflow has a fairly specific rubric for judging questions, and a central part of it is the requirement that they have a single verifiably correct answer. The example question does not, and it runs afoul of the guidelines in multiple other ways. The example question is something for a conventional discussion board or mailing list - it's not a good Stack Overflow question.
Also, whereas you're like the fourth person here to say the questions must have a single answer, that requirement is not called out in the SO guidelines at http://stackoverflow.com/faq. The closest I see there is "You should only ask practical, answerable questions". A question asking for pros/cons of storing images in a database (vs. links to files) meets that criterion in my book.
(They have decent transcripts there)
Jeff & Joel talk about the concept of what makes a good question a few times -- the way they got to there is interesting and worth listening too. Actually, the whole series of podcasts is an interesting view into the thoughts of founders starting a company.