You may as well ask why they'd hang out with the awkward, motor mouth chubby kid. I saw the Monster Squad as a group that isn't well liked by most of the other kids. The core members definitely seem to be Sean and Patrick. Likely it was originally just the two of them. Horace and Eugene were probably let in because they were the only other kids who wanted to hang out with them and/or shared their love for monsters. They're all four the social misfits so they stick together, united by their mutual appreciation for monsters. Friendship, true friendship, can be unusual.
Rudy was the only one who seemed to be respected by other kids, and he only joined because he was invited; he'd never offered to hang out with them. And the only reason the invitation was extended was because he made E.J. stop picking on Horace. I got the impression Sean and Patrick knew Rudy casually beforehand, but they'd been afraid to approach him and he'd been aloof (or at least distant) enough to act indifferent towards them. It took the incident with Horace to make them realize he wasn't like all the other cool kids, so they worked up the nerve to go and do more than just say hello; to invite him into their little circle of friends, and he figure, why not.
That's my take.
I mean, really, how many times will you look under Jabba's manboobs?
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