Corrected entry: Lucy's dad brings up the idea for her to paint his shed. The script should have had Lucy wanting to do that on her own - without that prompting there'd be no need for them to bother repainting it every night, which they clearly don't enjoy doing.
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Correction: Lucy's dad and brother go to great lengths to re-enact everything that happened the day of the accident, including having Lucy paint the garage. They don't really want to do any of the things they do on that day, including eating the cake and watching The Sixth Sense.
BaconIsMyBFF
But why wouldn't they just go and pick the pineapple instead of dad prompting her to paint the shed? Then he wouldn't have to paint over it every night.
Because painting the shed makes her happy. They are sacrificing their time and effort, at great exhaustion, to keep her happy.
BaconIsMyBFF
Going to pick the pineapple puts them in public and gives a much greater chance of her finding out the secret and having a bad day.
LorgSkyegon
It absolutely does, and it does lead to some issues when she gets pulled over for expired tags. Dad and brother's plan was not very well planned out and certainly wasn't smart, but that doesn't constitute a mistake in the film. People make poor decisions all the time.
BaconIsMyBFF