It's an incredibly complicated question that can be asked so simply: How much should the BBEG know about the PCs?
It's a major issue I'm running into right now in my campaign. The story has taken place over about 6 years of in-game time, wherein the PCs have progressed from level 1 and will finish at level 20 (they are level 18 now). They've handled everything from wandering goblin bands to mighty great wyrm red dragons. They've done personal quests and they've saved kingdoms. They've collected (and returned) artifacts and they wield a stunning array of incredible magical gear.
Many of the PCs are renown figures in their various homelands, with one being the general of one nation, a diplomat for another and an honorary chief in a third. One is seventh in line for an imperial crown and another is second in line (for separate nations). Only one hides her actions and whereabouts actively, but she is well known in certain regions, where she is held as a mighty hero.
So, though my BBEG was picked and roughly built by the time the PCs hit level 10 or so, his encounters were not, which is what brings me back to my original question: How much should the BBEG know about the PCs?
Clearly, it's been building towards this final encounter for some time now, and the BBEG is actively trying to pick off the PCs before they can get to the final showdown. So how much should he know about the PCs strengths and weaknesses?
Simple tactical things like "they are weak on ranged attacks, so keep your distance" or "the many went for very high AC, circumvent that" and other basic things like "high level casters are more dangerous than high level fighters, so attack them first" are obvious. But should he know that one fighter has a really good Will save while another doesn't? Should he know that the wizard often prepares spells specifically to counter certain nasty conditions (but not others)? Should he know that the party's cohorts are specifically trained in certain tactics (namely grappling) and to counter that?
The BBEG is a summoner who focuses on binding various fiends. The players know this and so they have built themselves with holy weapons and a good array of anti-fiend spells. This isn't going to change. Those will still be there to reward the players for paying attention to the clues that were dropped earlier in the game.
But should his eidolon (which he can change fairly often) be built to specifically lock down certain characters? Should he have magic items tailored to block specific strategies the PCs have used? Should he have specific minions hired/summoned/built/necro'd to foil the party?
Basically, I want to build a memorable and challenging set of encounters for the players centered around a very intelligent bad guy, but I also don't want to pull the rug out from under them either (especially after more than 3 years of playing the same campaign).
So... thoughts?
If he is smart, pretty much everything. If he has researched them and had spies follow them, he knows what they can do, what their tactics are. Remember, the renown means people sing of their deeds - all the details will be there in the song, for him to hear.
So yes, if he is even moderately intelligent and knows they are coming, tailor him to meet the challenge as best you can.
If he's into fiend-binding... even lowly Imps have Commune once a week. Judicious use of simple yes/no questions over time can accumulate a LOT of knowledge about the PCs. For instance.
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Most battles have witnesses. Not to mention there's an entire school of magic devoted to spying on enemies - any 20th level enemy should have access to level 9 divination spells.
He should know everything about the PCs up to and possibly including their deepest, darkest secrets.
Don't worry about "pulling the rug out from under them" - at level 20, if you're not prepared for everything, you're not prepared for anything.
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He should know everything. Everything.
To avoid the PCs being upset about this, find some way to reveal to them that he knows everything, and possibly how he learned it. That'll avoid it being a nasty surprise that he knows them, while still letting him plan intelligently (and letting his actual tactics surprise them).
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Think E! True Hollywood Story.
He should have intel on them even they aren't aware of. Every action they have taken, every foe they have defeated, it's all known to him.
A 20th-level BBEG will be ready for everything they are able to throw at him, and will gloat about it.
Just don't let him start monologuing.
I recently have come across this issue recently. The game I run has a good balance of characters and they are currently 11th level. They have similar accolades. Since they are eventually going to fight to save the prime material plane, they will be famous to most and infamous to others. My BBEG has knowledge of the group and has sent groups of merc's and assassins to derail them. Of course, my players are very smart and have been able to continue with their quest(s).
Now, since the BBEG has been a part of my game since the beginning, they both know a lot about each other. The BBEG has spies, allies, and cohorts who report to him. He also had bards and seers at his disposal. Now, to be fair I allow the players to do the same. I love dropping intel on the BBEG, but I don't give it all away on the first date. The players get excited knowing a little bit more about the BBEG, his allies, and enemies. They immediately start plotting and scheming.
I hope that helps you and let us know what you decided to do!
I've done a lot of thinking, planning and talking with the players. We all basically agreed that the BBEG should be incredibly well informed. Between his contacts, spells, minions and just the sheer fame of the PCs, he's going to know just what to do. I've basically decided that he's going to know everything on their character sheet, as well as all of the things they did while on the Prime (there were a few extraplanar adventures) up until they head to face him. This basically means that he won't know what new gear they bought for level 20 and what new spells they might have picked up, but that's about it.
However, it was agreed that his high level lieutenants should not be built to counter the PCs, but should be built as fully autonomous characters. I liked this and, as much as possible, have tried to build them in a vacuum.
Since the BBEG is a summoner, however, bringing in specific things from the bestiaries to specifically counter the PCs was considered kosher. Some of the PCs are very good at knowledge checks and I'll probably let them do some research before going in to get some warning.
The adventure isn't for another month or two (still have levels 18 and 19 to get through), but I think it will be fun.