I wonder could it have been written a bit more realistically? Maybe Kevin's brother had a timeshare in it (he seemed to be doing well) but couldn't make it that summer so the gang used it instead, but only for the 2 weeks or whatever that Casey Affleck would have had it for.
One of the stand-out scenes - the one with the 2 girls - would have to be worked into it some other way - maybe they're in the next house along. Also not sure how realistic it is that they get jobs as house painters in an affluent area so easily - can't imagine any of them being all that at manual labour, and wouldn't that particular job require some training/qualifications? Even if not, I can't help but feel for any trade school/self employed painters and decorators being denied work so that these students can have summer jobs to fund their partying.
Also, is it ever explained why Vicky and her friend are at the shore too? Or are they not and they just drive up to visit occasionally?
I'd also be curious if they did the same thing in the summers of 2001 and 2002? Maybe not as Jim and Michelle got more serious and Heather probably wouldn't have been abroad again so Oz would have spent most his time with her.
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