All swell ideas but sadly won't work.. Kinda gauged my players who don't metagame and a big part of the appeal wasn't just getting the keep, but getting the keep and getting stories to tell about the wicked things they fought in order to gain the keep.
"And this is the room where we had to slay no fewer than FIVE owlbears. And you won't believe what we had to fight in the dining hall!"
So this kind of needs to be a dungeon crawl more than a morally gray area.
Anyway, this session got a last-minute cancellation (family emergency) so with two players... they were kind enough to focus the session on very non-combat oriented things.
Starting with the relentlessly chaotic ranger taking a quick step off to try to find some drugs to slip the rest of the party during a feast thrown in their honor. She asks the first shifty guy she spots... and he immediately recognizes her as a totally easy mark.
So one quick alleyway transaction she spends... god, 500 or a thousand gold or so on about 75 gold's worth of a cooking spice called fusaka (blatantly stolen from Critical Role so the other ranger's player, a big CR fan, can be in on the gag). And at the feast she's trying to think of a way to slip it to people and inquires with the dwarf cook party tagalong (old friend of the bard character) who's just excited at the fact that she bought some, so she starts putting some on the others' meats, and the cook and the halfling sorcerer NPC filling in for an absent player are discussing the spice casually and it STILL hasn't dawned on the player that she got played until dessert time and it hasn't affected anyone.
So she tries to get revenge... takes the other ranger with her under some false pretenses ("I got mugged!"), they find the tracks of one of the people, wait until it's even later in the evening before striking the house where the trail ended... fail their stealth checks, an old lady comes out of the house and starts berating em and a few failed deception checks later the chaotic ranger decides to tackle and try to punch the poor middle-aged lady. Botch, punches a rock instead, breaks the grapple, so now the other ranger jumps in, and one of the swindlers jumps out, unaware of who's causing trouble but just knowing his aunt is being harrassed... so he runs to the streets and shouts for guards. Players hightail it out of there.
THE NEXT DAY
So, one thing down... Now the players are once again figuring they'll take on RP and skill check tasks to lighten my load encounter-wise. Chaotic Ranger nabbed some bounties off a bounty board in a seedy part of town the day prior.
Out of the three, they took interest in two. Apparently the fierce half-dragon warrior, they realize he's clearly out of their league. But not the Wolf... Whom they know nothing about. Even the bounty post is nebulous. Really the only bounty that's worth taking and succeeding at doing at their level is the dwarf barbarian who's wanted for owing some money. But the Wolf. Man they want him. They'll never get him. He's a master thief, a gentlemen thief, a thief who meticulously picks his targets, what to take, plans everything against every eventuality... and only takes the ill-gotten gains of the corrupt rich. IE the stuff that they couldn't even report as stolen by the authorities.
Anyway, so they try to inquire in some seedy parts of the large city, find a gambling den... go in with a plan. Two of the party members will go in as hotshot high rollers, the other two, Chaotic Ranger amongst them, will play servants/slaves... And then everyone but Chaotic Ranger is just meant to hang at the gambling tables while she pokes around and tries to use Thieves Cant to get info, but all she can say to gain the attention of people who'd understand the language is "gee I sure hate my boss (ie Other Ranger) wish someone would kill him" which only gets a supposed assassin to offer to take the hit, so she has to backpedal quickly. Then she tries to sneak in the upper floor that's members only, fails the check, and gets thrown on her broccoli.... Then goes back to the bar and outright ask the bartender about the Wolf. One secret signal later and she first, and then the entire remainder of the party, go Jazz out the Banks house.