> There are a lot of things wrong with this analogy

I think so. As a rule, when something can be developed incrementally rather than planned and engineered, it should be. This makes mistakes less expensive, allowing you arrive at a satisfactory end result in a fraction of the time.

This is one of the huge advantages of the web over desktop software. Initial delivery to the desktop and subsequent updates cost significant time and headache. Redeploying to the server is just a matter of running a script.