Living in Dallas, I see a lot of Mark Cuban, and I think the pros and cons break down like this:

PROS
1. There's no question that winning is extremely important to him.
2. He had a reputation as a meddler at first, but he seems to have either a) scaled back his interference, or b) learned very quickly on the job. After all, look at the success the Mavs have had pre- and post-Cuban's purchase; there's no question that he made a drastic, positive change not just in the way the team is perceived locally and nationally, but also competitively.
3. I know for a fact, not just from his ownership of the Mavs but through professional experience, that he very much embraces not just new ideas but also fundamentally new ways of thinking. I think one of the results of this is that the Cubs' front office would be strongly encouraged to become far more innovative in terms of player evaluation and roster construction under his ownership.

CONS
1. The Cubs are not like the Mavs, in that they're not completely moribund as a franchise, and don't need bold changes to make people care.
2. Cuban embraces the obnoxious in terms of game atmosphere. Music during the game, overbearing PA announcers, etc., are all standard at Mavs games. It's true that that's the norm in the NBA, but I'd worry about the game experience at Wrigley taking a turn for the worst.
3. He is, for better or worse (and it's usually some of each), a lightning rod for controversy. Some of his lesser moments have been bad for not just the team but the league. For example, his complaints about officiating, which got so out of control that he once intimated that the outcomes of games were fixed.

I don't think there's any question that the good has outweighed the bad for the Mavs. Whether it would for the Cubs or not is hard to say, but it's a chance I'd take.

I'll add that I think the whole point is moot. Even if he wanted to buy the Cubs, I think it's extremely unlikely that MLB will let him.

I'd proably take the chance, too, but the fact that "Cuban embraces the obnoxious in terms of game atmosphere" really worries me.

Mark Cuban was a guest on Comedy Central's The Colbert Report last night, and flatly stated that he does not want another sports team.

More specifically, he said that his wife would leave him if he bought another one. Being on Comedy Central, that part may or may not have been a joke, but he seemed serious about not wanting another team right now.

The idea of selling to an individual is fraught with peril. Chicago needs to own the Cubs as its own team, just like Green Bay owns the Packers, i.e. its people do.

Respectfully,
FEARLESS BEAR