Also this will be less of like, explanations of teams, and more little trivia, headcanons, and character relationships.
Eevee is a very common starter Pokémon in...Middle earth region (idk), due to its popularity in breeding, their easy to handle for children, and the many evolution possibilities. The bardlings, Sam and Frodo, Legolas, Bard, and Thranduil all had an Eevee as their first Pokémon
Sam and Frodo's Eevees were particularly close, and even evolved into an Espeon and Umbreon just minutes apart.
Aragorn and Boromir both started out their respective journeys with a Honedge, and it's the initial source of their friendly rivalry. Their strats with Aegislash is wildly different however, as Aragorn depend more on the blade form while Boromir leans on the shield form more
In their youth, both Elrond and Galadriel dabbled in Pokémon contests before taking on their respective gyms. Both still keep up with the scene even years later, and both are quite intrigued by the curly haired upstart with his Gogoat
Almost everyone in the region knows that gym leader Sauroman and professional nuisance Gandalf are divorced, but almost no one has any memory of the two of them actually being married. Even people in their age range only ever remember the two as divorced. It's one of the many anomalies surrounding Gandalf Gray.
Mirkwood is not the actual name of the city, but Greenwood. Surrounding the city is a thick forest, populated mainly by mean spirited fairy and dark types, that drove away most of the grass types that kept it, well, green. The forest became a creepy and dark place made to get lost in, so it gained the nickname of ‘Mirkwood’ most inhabitants of the city dislike the name strongly, and sees it as an insult.
Many young trainers fear entering the forest due to how easy it is to loose your way in it, and how dark it is even during the day. This is why Illumise and Volbeat are very popular Pokémon around that part of the region
Despite being generally unhelpful and sometimes a bit grumpy, Gandalf is extremely kind to to everyone he meets, and does see the potential in everyone. The one exception to this is Peregrin fucking Took, who he for some reason is extremely hostile and rude towards. Pippin takes this as a compliment
Champion Lobelia Sackville-Baggins team consists of six Alakazams, all of which can mega evolve. I am committing to this bit
Bard Dragon retired around the time Bain was born, wishing to spend more time with his family. He was, to no one's surprise, a Dragon specialist, but in current day he only still has two of his old team with him, his Hydreigon (Was a Zweilous back during his gym leader days), and his Goodra.
Aragorn and Legolas are childhood friends, and have always traveled together. They started traveling with Gimli when they reached Erebor city, and needed a guide to navigate the mountain, as it's easy to get lost. He just sorta stuck around after that.
So far Aragorn has had run ins with Ho-Oh, Raikou, Celebi (Twice!), Shaymin, Arceus (That was an experience), Victini, and Zeraora. He has no idea as to why they are so drawn to him.
Merry and Pippin caught their Zigzagoon's and their Plusle and Minun entirely separately on different occasions. They're a little bit pissed that they have matching teams, as people mix them up enough already.
The Pokémon professor of the region is an odd fellow by the name of Tom Bombadill. No one knows what he’s studying, no one knows what his deal is, but he is in possession of several legendary Pokémon so no one really fucks with him.
