Are there really rules against him distributing information to the outside world via friends or his lawyer
I think you may have misread:
The penitentiary also threatened to (list of actions) if he tries to communicate with the outside world via Internet again.
They don't object to him communicating with friends or his lawyer; they don't want him active online.
What is the point of such rules? For some stupid edge-case of suppressing mafia bosses from operating from prison?
That's what comes to my mind as well. Weev isn't a mafia boss, but he is a black hat hacker, and he is (was?) a part of Goatse Security. The Internet is his medium. If you throw him in prison and grant him free access to the Internet, have you really done anything? It's actually kind of an interesting conundrum- a thief is removed from the streets to stop him from thieving. Here we have a hacker we have tried to put into a system meant for a thief, when maybe the better analogue would be to remove him from his streets, i.e. the Interenet, instead of putting him in prison to remove him from the street.
House arrest and monitored or limited access to the Internet has always seemed like one of the better options the penitentiary system has tried for "Internet criminals".
How? I thought that the Tweets weren't directly from him, but were posted to Twitter at his request by friends that had his credentials. So he's not allowed to pass messages to friends that are then distributed to the world via Twitter?
I disagree. His friends could communicate on their own with the internet, saying "This is what Weev said when he was talking to me...", or in some other way make it clear that it's not weev talking to the outside.
That would likely still piss people off and get him in hot water, though.
I think you may have misread:
The penitentiary also threatened to (list of actions) if he tries to communicate with the outside world via Internet again.
They don't object to him communicating with friends or his lawyer; they don't want him active online.
What is the point of such rules? For some stupid edge-case of suppressing mafia bosses from operating from prison?
That's what comes to my mind as well. Weev isn't a mafia boss, but he is a black hat hacker, and he is (was?) a part of Goatse Security. The Internet is his medium. If you throw him in prison and grant him free access to the Internet, have you really done anything? It's actually kind of an interesting conundrum- a thief is removed from the streets to stop him from thieving. Here we have a hacker we have tried to put into a system meant for a thief, when maybe the better analogue would be to remove him from his streets, i.e. the Interenet, instead of putting him in prison to remove him from the street.
House arrest and monitored or limited access to the Internet has always seemed like one of the better options the penitentiary system has tried for "Internet criminals".