Money-wise, I realized it's easily do-able to afford the Swift Sail pre-Dragon Roost Island. By the time you get to Windfall Island (including quickspinnning the flowers near the two girls), you will have around 175 rupees. This includes getting the chest under grandmas and quickspinning the log on Outset. 30 rupees reside in the Battleship Game shop behind the counter on Windfall. In addition, chasing the kids around will yield 50 rupees once you've talked to the teacher. This puts your total at around 255.
Minus 80 rupees for the sail, and you will then be at 175 rupees. On Cosmo's recent stream (http://www.twitch.tv/cosmowright/b/472330873), using a technique of rapid bidding (about 12 rupees over the current bid) can get you the Swift Sail at 162 rupees (or less since he made a small error).EDIT: Wait.... is there any way to make it night time on Windfall Island pre-Windwaker?
EDIT2: Why not sail out of Windfall Island quadrant, pick up some rupees and loop back
EDIT3: Fuck the wind is forced east. You wouldn't be able to come back unless you headed North.
EDIT4: You can't head north or south due to quadrant restrictions
EDIT5: Sail to Dragon Roost Island and pick up Rupees from Barrel Game until exact moment of night, then savewarp back to Windfall?