It's one of those douchey terms used by Yorkies, Rastas, Moors (no disrespect to the latter two), and other so-called conscious people in an attempt to sound smart, smooth, above it all, etc. All it is is putting a cute spin on "understand," that's it. This word is a plague and the user can't hope to possibly be taken seriously.
And to correct another entry on this word, no, the Five Percenters do not use it, as any 5% worth his salt knows better.
Once again, it's cute and quite slick as slang, but only a fool would have "overstand" in the repertoire for serious discussion of anything.
Overstand these nuts.
"Do you overstand me, brother?"
"What the hell does 'overstand' mean?"
"..."
"Man, where did you even get that from?"
"Uh, ah..."
"What are you, Boyz II Men?"
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