I hesitate to say which of my apps was easily the most annoying, hands-down, since it's still pending and this is my real face you see to the left. But DAMN, it was annoying. Half-meg limits on documents! Doesn't allow a CV (how am I supposed to describe 26 years of work experience without one, pray tell?) but expects individual fill-ins of each employer. Just picking the department was a 20-minute struggle (because rather than a standard drop-down it has a bizarre bug where the provided list keeps jumping before you can click your option). Also, a radio button I inadvertantly clicked could not be erased! This option was not offered. Instead it demanded that the rest of the entry be filled in, no matter what. Finally (on deadline day) I gave up and filled in a fake third undergraduate school called There Is No Third School.
Berkeley featured the nicest application software. The rejection letter was also very polite.