Nas and Eminem both come to mind as two artists that hurt themselves by releasing wacker material on albums like I Am and Encore because it hadn't leaked and left better songs off their albums because they had leaked. They would have ultimately been better off releasing the stronger songs, bootlegged or not.
Back then, a bootlegged album hurt your sales because everyone had it before you released it. There was no need to pay $16 at the record store for an album if you were able to get a copy for free. Even if the quality was worse, it didn't matter. Sometimes, bootlegged albums would have songs that the retail version didn't, so you would be paying for tracks you don't even want to listen to.
Illmatic and The Eminem Show were both bootlegged. That's why Illmatic only had nine songs and didn't sell as much as it could have, and that's also why The Eminem Show was released earlier than planned. Eminem was pissed when TES leaked and he didn't want to deal with it again with Encore. That album could have been better even with the leaks, but he was popping Valiums like Skittles back then.
As far as I Am..., I think Nas just gave up on the double album idea and rushed to get it done because Columbia needed it finished ASAP. There's no official tracklist for the double album because it was never finalized, and there's no chance Nas remembers it at all. I'm always going to wonder what I Am... could have been, but then I remember that "Dr. Knockboot" was one of the bootlegged songs and "Nas is Like" was recorded at the last minute. Maybe things turned out the way they were supposed to.