My current campaign has the party in the Silver Marches of Faerun, traveling to Silverymoon. I've introduced a couple of plot lines for antagonists including a dread necromancer with an army of undead, orcs moving throughout the area preparing for another war, and a slaver backed by the Zentarim with a vendetta against the party (because they put him out of business in one location). I need to point out that the party is predominantly evil, a former krewe of a thieves' guild, and they wouldn't face up to evil just because it's the "right thing to do." After all, they are evil themselves. Therefore, building a challenging non-player character (NPC) they would want to take down is a problem. Here's how I built one, from concept to completion.
The slaver aforementioned had a sidekick named Urnig. Urnig was a particularly interesting half-orc, with 5 levels of rogue and 1 level of swashbucker (Complete Warrior). This particular half-orc had been a particular problem for the party, taking one of the members captive and then doing unspeakable things to him. Then, to make matters worse, he was brought back from the dead as a zombie to wreck havoc anew.
I wanted an NPC that would cause the party some trouble, but not so much that any of them would be in extreme peril. I also wanted a hook that would cause the party to have this BBEG. I decided upon a brother to Urnig, this one full human. Urnig would be the younger brother, after mom was raped by an orc (the BBEG of the clan, but that's a story for a different time). The connection with Urnig needed to be enough to cause the party to want to do something to said NPC, especially the one taken captive by Urnig. But I did need this one to be a bit of a challenge, so I had to think carefully about how to make the NPC last more than a round or two.
First and foremost, I knew I was dealing with a party of rogues. The highest level was 6th, and given a chance, that rogue would take advantage of a sneak attack from surprise. Given a particular magic item possessed by said rogue, that meant my little antagonist could have been knocked off on the very first strike. One way to prevent this is to ensure the NPC had uncanny dodge, which one gets as a Level 4 Rogue. Given that the highest level of the party was 6, that meant none of the party members was going to get sneak attack damage due to surprise. Flanking sneak attacks were still okay, which was fine. I wanted the group to engage him because one-on-one he could be deadly.
Second, I wanted him to be good at single combat, but I didn't want the typical fighter. The swashbuckler class came to mind, especially since I do have a bunch of rogues. Not all of them have magical rapiers and if I gave the NPC one, that would add another to the group. They were set on armor (at least, light armor), which made that class more feasible. However, since I wasn't going to give the guy much in the way of armor, I needed to beef him up a bit on hit points. This led to Swashbuckler 4. He would have weapon finesse, he would have insightful strike, and he'd have a couple of levels of hit points of advantage on the group.
Third, I wanted him to have some nice items, but I'm always very careful about what I give the party in the way of magical items. Magical rapier is a given and so that's not an issue. But what else? I had already ruled out armor, so a minor cloak of displacement seemed fitting. Most of the world wasn't going to be able to stand against a rogue 4 / swashbuckler 4, but if I didn't give him something, the party would toast him right away. The displacement cloak has a 20% miss chance (meaning 1 in 5), and it's not too powerful. It's also something the sorcerer in the party could probably use. That's about all I wanted to outfit him with because anything more and he could prove too much for the group. They were all 6th levels and I'm looking at them taking down an 8th level NPC, albeit without support. So with that, I drew a close on magic items.
Last, I had to give the character some personality. Also, I needed to give some reason he would have to come after the party. After all, this was a half-brother who was a half-orc. Given normal stereotypes, he wouldn't care. But the combination rogue and swashbuckler screams "pirate" and the brother had magical items. Plus, the party knocked over a small slaver's HQ. That means they likely had some goods he could get. A few days travel and he'd get a lot more than after months of pirating. Given his half-brother was a half-orc, I could see the fully human brother thinking the half-orc was stupid and the party just got lucky. Plus, he's used to bluffing his way through fights. Given the reputation of the group, that opinion is justified, though completely unsound.
How did the group handle the NPC? Not as I expected. You can read about it here (On to High Hold) .