So Lando does the walk of shame out of the Pokémon Nursery and encounters a Gentleman with a Sableye. This battle is surprisingly lengthy, due in part to the Gentleman using a Full Restore. Man, between trainers using restorative items and wild pokémon often calling for reinforcements every other turn, even the most nondescript battles turn into high-stakes affairs. Anyway, this battle further showcases Vampiris's worth and allows Scotty to evolve into a Herdier with the Sand Rush ability.
Moving on to Route 5, Lando runs into Hau being bullied by some edgelord named Gladion who's apparently a Team Skull reject. Odd, given that he actually has more powerful pokémon than the grunts. Joan Jett and WendyWhallop make short work of this Gladion fool and his Type Null, rendering him even more sullen.
Lando has a reason to be sullen now too. His first "new" encounter on Route 5 is a female Metapod (level 15) but it faints before a PokéBall can be tossed. Although the majority of Lando's encounters on Route 5 are pokémon he already has and a Metapod would more likely be dead weight, it would have been nice to have another pokémon for the team.
Another reason it would have been nice is because on the way to the Route 5 Pokémon Center, Lando encounters two Rising Stars who want to engage in a double battle. Lando launches BuzzLiteyear and Joan Jett against their Vullaby and Rufflet. Lando gambles with having BuzzLiteyear attack with Spark before switching out, and then has Joan Jett use Rock Blast to take out the birds. Unfortunately, both Vullaby and Rufflet draw first blood and kill BuzzLiteyear due to a type advantage.
Akala Island has not been kind to Lando at all, and he continues to curse his bad luck, the frustration of which leads to poor decision making. Tapu Lele, the guardian of this island, seems to have it out for Lando. Don't bet the Millennium Falcon in a game of Sabacc now, buddy.
Lando's luck needs to change, and soon! Right now, the only companions he has are Bam Bigelow, WendyWhallop, Joey, Vampiris, Joan Jett, and Scotty.
Well, the next new area is Brooklet Hill and Lana's Trial. Lando, out of respect for the law of the land, will refrain from catching any pokémon in Brooklet Hill until after the Trial is over. So Lando follows Lana around Brooklet Hill and eventually encounters Totem Wishiwashi. Lando is confident in Vampiris...but Totem Wishiwashi's Soak and powerful Water Guns put Vampiris's HP in the red! Even her Mega Drain doesn't do much damage. Thankfully, Leech Seed and (especially) Magical Leaf do the trick, and Totem Wishiwashi goes down after a tense standoff. But with Vampiris's HP low and a companion Wishiwashi still around, Lando switches out for Joey, who finishes the job with a Hyper Fang. Lando survives by the skin of his teeth here. It's incredibly lucky that he didn't lose his only Grass type, who's become a keystone member of his team.
The trip to Brooklet Hill has given Lando a new PokéRide Lapras, a Waterium Z, a fishing rod, and two places to catch: Brooklet Hill and Brooklet Hill Totem's Den (both differentiated by Green Waves.) Captain Kiawe's trial is next and he specializes in Fire Types, so Lando definitely needs to catch a solid Water Type here. But, for now, he accepts Lana's offer to warp him back to the Route 5 Pokémon Center so he can enjoy a mug of Komala Coffee and relax before "going fishing" at Brooklet Hill.