I'm really not sure why the quest rule still exists, but it in fact doesn't work. Checking it does not cause you to start with 999 rupees or seem to have any impact on your quest whatsoever. I'm pretty sure that I should report this as a bug since the other obsolete quest rule (Link starts with full life) does still function, and while I don't have any quests old enough to check it out, it might have damaged backward compatibility.
I'm sorry if this was an unnecessary bug report, but it's not good to have check boxes that say they do something when they don't anyway, right?
Absolutely. I'll look into it.
This bug persists in b550 (not using 557 since it's nothing new).
Whether this is relevant or not, I'm not sure, but I believe the rule was intended only to give you the Giant Wallet which granted you the ability to hold 999 rupees, not 999 actual rupees themselves. I'd need to test it to see if you still get the Giant Wallet with the rule, but I propose it be scrapped altogether since it is entirely covered by Init. Data.
The Quest Rule only gives you the Giant Wallet. I know this for sure.
This quest rule no longer exists in b564. I guess that means this bug is dead.