For N64 owners looking for a serious hoops simulation, this season has yet to show any clear winners. NBA Live 2000 is horrid and the jury is still out on NBA Jam 2000. Courtside 2 isn't terrible and does sport some truly interesting features like personal player development, but I can only marginally recommend the game as it is with all its flaws. In fact, if you don't mind slightly dated graphics, I would actually suggest (if you haven't already) playing the first Courtside which is less buggy and more playable.
As for fans who like their basketball action fast and loose, don't be fooled by Courtside's supposed 'arcade' mode. Like the one in NBA Live 2000, the 'arcade' mode in Courtside 2 is unconvincing and uninspired as computer AI will not react differently to the lack of rules and dominating it should be no problem. I'd stick with NBA Showtime for this type of shtick instead.
Then again, if system loyalty is not a factor, and money no object, then those of you who consider yourselves hardcore basketball mavens, go pick up a Dreamcast and NBA 2K. It's my pick for this year's best game of video b-ball.