I can't even tell how many times I've beaten this game already, but it must be dozens. I still enjoy it, that's the amazing part.
But since it's my umpteenth playthrough, naturally I've been looking at the game with a more critical eye, as well as doing things a bit differently. Usually, I'm a sensitive and sentimental goodie-two-shoes, though my female rogues tend to be more on the evil side, but nothing overtly vile. Mostly, they're a villain with good PR, playing a hero part because it pays off. I know this has been done to death, but there's some real strangeness in the game once you try to be more evil than that.
For example, you can side with Firkraag and get him the ownership deed for Windspear Hills from Garren. I've pickpocketed it, so I don't know what happens if you kill him, but either way, siding with Firkraag means that Garren's child is killed in the cell. This triggers no reputation change whatsoever, while killing Nalia's loathsome aunt, where no-one sees it and where you could easily lie she died in the attack, gives you a heavy rep hit. This is very odd. Also, once I delivered the document, everyone in the party except for the PC
got a nice chunk of experience (this may be a bug?), but the reward was a crappy cape.
On the other hand, it was rather refreshing to have a band of heavy knights appear and hack at us on the street when our reputation reached 1 (long story short, Valen The Vampiress That Constantly Gets You In Trouble). But the rewards are usually not worth the trouble of going evil, which is strange.
Anyway, it's crazy how on an 20+ playthough you can discover new things, albeit little ones. After disposing of the Eye Cult, for example, you can be ambushed in the temple sewers by beholders. You can rat Hendak out to Lethinan and the slave trade continues throughout the game at the CC. Even better, you can rat out Phaere to her mother (I didn't know that!) and watch her get executed... then turn on Ardulace who foolishly invites you to the ritual chamber. Or sacrifice the silver dragon eggs for your own gain. (Again, the reward is not worth it at all, but it's better if you have Valen with you.)
Oh and I finally tried romancing Viconia, whom I sometimes take along but I don't really like the character - it's a good idea (clinging to her past glory and definitely not an atoner), but wasted in execution. So far, the romance is horrible and utterly unappealing, which I thought was Jaheira's turf. Honestly, it can all be summarized as "she's a DROW! Are you drooling already?" I was expecting something better.
So I guess what I'm trying to say is, damn it's a good game