Nearly every playthrough I do a lot of the same things. I generally dump strength on Charname because I know I can buy the belt of Hill Giant Strength from the Adventurer's Mart or get the Gauntlets of Ogre Power in the Planar Sphere. I know I can do this, so I skip the strength potions. My sorcerers never learn strength and my clerics rarely memorize Strength of one (It's actually a debuff a lot of the time).
If I'm taking Keldorn, I usually take down Firkraag pretty early on for Carsomyr, I almost always grab Daystar the first time I'm leaving the city. My Kensais usually specialize in katana's because I know I can pick up Celestial Fury pretty early on by cheesing my way through the Guarded Compound. I buy up the Shield of Balduran before heading to Brynnlaw so I'll have it for the Underdark, I always go back to sea instead chasing Irenicus through the portal because I don't want to miss the Cloak of Mirroring and Wave Halberd part (although I just about never use it, except maybe if I've got Dorn).
What if I couldn't count on these things though? What if Ribald had Gauntlets of Dexterity instead of the strength belt this time? What if Firkraag dropped The Answerer (a seemingly fantastic weapon which I never use because you don't get until almost the end of TOB) instead of Carsomyr this playthrough or a new weapon of a similar power level?
I was doing some thinking the other day on what could be done to make my next playthrough feel a bit fresher, and I think a little randomness or uncertainty could be the ticket. I've been feeling the urge to do another run through lately, especially with all the cool kit mods people have been making.
I think it'd have to be done intelligently and would take a lot of work. The way I'm thinking this would work is we'd make some loot lists, separated by power tiers - you don't want to go to the effort of slaying Firkraag for a +2 Quarterstaff instead of Carsomyr, that wouldn't feel very good. It also wouldn't make a lot of sense for the Beastmaster at the Copper Coronet to drop the Ravager instead of the Tuigan Bow (Off topic, but this weapon is pretty rad with the Enchanted Weapon rework).
Basically here is how I'd see this working. We make a list of 5 or so items that are similar power level to Carsomyr. We write some weidu code that removes Carsomyr from Firkraag and then adds one of these 5 items to him via a random integer and a series of if statements. We do the same thing with many other iconic items of the game.
There would have to be a lot of exemptions of course, such as items that are important to quests and such, I'd also advise against removing the Red Dragon Scales from Firkraag because where else would you get them? It would also be more difficult to do with some items, celestial fury for example: Removing it and replacing it with say, a powerful +3 axe would mess up the guarded compound fight as Koshi uses Celestial Fury pretty effectively against you and he wouldn't have the proficiencies to use said axe, so maybe instead we remove Celestial Fury, give him a +2 katana to replace it, and give the Axe to one of his teammates who can make good use of it.
Anyway, this is just an idea I had. I'm really interested in what the community has to say about it both to gauge interest and because I'm sure you guys have some smarter ideas on how to go about it, heck for all I know someone's already done something just like this. I am moving this weekend so I won't have a lot of time to check this thread and/or work on it, but I will have some time in the next two weeks.