If there is anything we know about Lando Calrissian in Star Wars, it's that he's an impossibly cool anti-hero; I daresay even cooler than that scruffy-looking nerf-herder Han Solo. Although the Baron Administrator of Cloud City became a key member of the heroic Rebel Alliance, he had a sordid past as a card player, gambler, con artist, smuggler, and overall scoundrel who would not hesitate to exploit loopholes to suit his purposes. Hence, Lando will keep Benny by shamelessly exploiting Alola's "Law of the Land" loophole.
Alola's geography is set up quite differently from other Pokémon regions in that there are fewer marked number routes, but each route is very lengthy and subdivided into several different, unique areas or sections (not always marked by signs) that spawn distinct pokémon. Ergo, Lando considers the Route 1 area dubbed Hau' Oli Outskirts as a distinct area where he can catch a pokémon. I'm certainly not the first Nuzlocker to encounter this conundrum, nor will I be the last to exploit this loophole. The game's overall structure itself challenges several longstanding Pokémon conventions, so I see nothing wrong with adjusting the Nuzlocke rules a little bit to account for that.
Lando and Lillie visit Professor Kukui's beachside lab where he and his Rockruff are, well, playing rough in the name of research on Pokémon Moves. Kukui gives Lando's PokéDex a Rotom-powered upgrade, gives him a special amulet to allow him to undergo the Island Trials, and... tells him to go to school first to learn Pokémon Basics. School?!?! Man, what a drag. Lando reluctantly goes to the school, squelches a bunch of kids there, and is subsequently called to the office. Lillie scolds him for being a troublemaker, but Lando shrugs, "Oh come on, girl. You know you like a bad boy."
The teacher who called Lando down wants to battle him herself. Finally, some real action against a powerful pair of pokémon: a Magnemite and a Meowth. Bennie is immediately switched out to avoid a serious type disadvantage to Magnemite, and Bam Bigelow is brought in. His Ember is super effective and fells Magnemite! The next opponent is Meowth, whose Bite docks 8-10 HP off of Bam Bigelow. We have a real cat fight going here, folks! But with some finesse, Bam Bigelow emerges victorious despite his HP being in the yellow. This was kinda exciting... for school... and Lando gets some Great Balls out of the deal. Nuzlocke Runs make even mundane skirmishes like this one into high stakes battles. Apparently this battle caught the attention of a pink haired Trial Captain named Ilima who promises to be a future opponent.
Finally Lando gets to explore Hau' Oli City with Lillie... until Hau tags along as a third wheel. The city itself is pretty neat, except for the fact that haircuts and clothing are costly right now and Lando would be better off hanging onto his money for pokémon supplies. Looks like Lando will have to earn his visible swagger the hard way before making it to the big league point where he can afford the dapper clothes and hip haircut. However, a nice lady in the city hall gives him a Revive, and since he doesn't need it for a Nuzlocke run, he sells it for 1000 PokéDollars to buy himself a fresh blue polo shirt. (Later on, he acquires more Revives from kindly folks and sells them to get a slick braided cornrow hairstyle to even further look the part of Lando.)
Hau' oli City actually has sections of tall grass in it, so why not capture a pokémon there, since the "Green Wave" counts this as a distinct area? Of course, it would be silly to walk into the first tuft of grass spotted in town. Just like when scoping out the ladies, Lando knows to bide his time, explore, and find the most appealing patch of grass.
While scoping out the town, Lando finds Trial Captain Ilima at the marina. While engaging in small talk, what should appear but a pair of Team Skull thugs? Team Skull is just too much. Those delightful guttersnipes never fail to amuse with their sick rhymes, ill dance moves, funky fresh theme music, and the way their eyes go cartoonishly wide when they lose battles. By the good grace of Tapu Koko, please let Lando survive this Nuzlocke Run long enough to get to Team Skull's stronghold.
After taking out those Team Skull grunts, Ilima challenges Lando to a battle test. I've heard that this encounter has unceremoniously ended the runs of skilled veteran Nuzlockers, so with this intel, Lando politely declines for now as he scoots off to hopefully prepare by getting a fourth pokémon in the city. He pokes around a few patches of tall grass in Hau' oli City, but all he finds are Wingulls. That is, until he spots an Abra in the tall grass across the street from the Pokémon Center and shopping mall! Unfortunately, despite throwing a Great Ball, the Abra breaks free, casts Teleport, and disappears, eliminating the opportunity of getting a Hau' oli City pokémon as a fourth teammate. It looks like Lando will be taking on the infamous Ilima battle with just Bennie, Pepper, and Bam Bigelow. Well, here goes nothing.