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I would totally get this for my mom. She loves garage sailing!
Maybe make the sail more prolific in the midst of all the other colorful funnery? nice pun, but make the pun more obvious i guess is what im trying to say.
i think you should do it maybe with a pirate flag next to the sail, because of the whole "one man's trash is another man's treasure" thing. Also the "sail-ers" are trying to make money.
The yellow really hurts my eyes....
awesome colors. 4