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Well this is a near-useless card then.
I believe the "in that territory" part is referring to "who" is targeted, not "when" they are targeted. If a player attacks from hand, the Hero is not affected by Broken Cisterns, but as soon as the Hero enters the territory, then it is affected from that point forward.
Broken Cisterns affects all characters in the territory while they are in the territory. If a new character enters the territory it is affected, if a character leaves the territory it ceases to be affected. So if a character leaves the territory and enters battle, while in battle it is not decreased, so Broken Cisterns will never trigger weakness.
Does he really drive a Fiat? I had envisioned him as a DeLorean kind of guy.
That's running quite contrary to what's been said before, with nothing but your fiat backing it up.
any official ruling on this?