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He always buys from Kelly. Maybe he's got a tab going.
He's physically paid for a couple of things, from Kelly and others. As far as Kelly goes, I believe he has a monthly tab with her; I believe one of the episodes has him paying it, though I may be thinking of something else.
On a related note, has he ever once been paid for his handyman-ing?
Probably off-screen. That way, the amount won't ever be dated. (Inflation Marches On?)
Or they pay him back with free stuff. I don't remember ever seeing him have to pay for stuff.
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