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I picked up my old Diablo II for a month or so - surprised to see a small community still playing. (I think a month is about the gameplay that D2 is worth before you get in to trying to see how many times you can do the same thing over and over every 5 min for your entire gaming session). I don't really recommend trying to box D2. Its all botted to death anyway, and there's not much benefit of boxing even if you do get it working (no follow command, so its all keyboard sync and running into corners every min or two to stay grouped).
OT: I boxed D3 heavily for some time, and i found that there's no point to boxing it in the end. The best method is owning 4 clients and leaving 3 afk in town while you clear Rifts with your main client. It's is faster then 4boxing it due the trouble of syncing your characters, and while they sat in town the whole time they are still able to port and loot the Boss when it's dead, and then you can loot share that way getting your main in really good gear.