Ultron: Tooltips aren't immediately visible to a new user. It's easy for someone to miss them. A help window that comes up straight away is in your face, and pretty much tells the user to learn about WinUAE before they jump into it. If they need assistance, they can always revert back to the hints. The hints don't have to be limited to usage. They can have helpful little tips like "Old EA games (around 85 to 87) usually require Kickstart 1.2 to run properly", etc. Basically, the sorts of things that you'd find on these forums, or in the wiki.
At the end of the day, it's up to Toni. If he doesn't want to implement it (and noone else steps up), then that's the final say