I'm personally okay with either one, however there's a lot to think about for either one

Like if it's together, you gotta think of the reasoning why, and how it benefits the story you're trying to tell

And if it's another person's OC, you first gotta ask them and you both have to think about how it affects both of their stories

Usually yeah. You gotta remember that other characters exist and try to come up with a reason, like a Gym Leader retires/Out of Town and uses them as a Backup, or a Champion getting defeated in the Championships, etc.

It all depends on your story and what you want to tell, but just remember about the other canon characters... Because well, they're canon!

Well you do follow a lot of people, so-

Ooh that's a tough one, Tyler hasn't had a Valentine's in a while but he does get some occasionally as a Senior.
The best he's probably gotten were some "obligatory" chocolates from Clair one time in a hangout session. Clair handmade it herself, so he cherished every bite

The Worst was probably being gifted some Flowers, which happened to be a bunch of Floette... That's how Tyler got chased by an Angry Florges the whole school day--

MERRY CHRISTMAS

And for Tyler, he normally settles down in his family home back in Blackthorn City. Mainly because he's constantly traveling and loves the warm family environment. One tradition his family does every year is help set up those giant city Christmas trees over in town.

The Gym Leaders Clair, and the other civilians help out as well and even some of the town's wild Pokemon! Afterwards, Tyler puts the star on the tree since he has Dragonite to help with that, and everyone stands around and enjoys a nice Christmas fest before events like Secret Santa happens

Tyler would participate for the Lols. It wouldn't be fun in the slightest-

I think I'd be pretty blessed if I was Boxy

Being the Easter Bunny sounds pretty good, and I get the best candy factory known to mankind through inheritance with adorable Rabbit and Chick followers who make sweets for me? I'd be sold

The only downside to it would be the Eldritch beings I have to fight every night because the Boogeyman wants the fear of every child... As well as boring meetings with other Holidays, but I can manage

It's pretty obvious, but Tyler loves a good Rollercoaster, it's always thrilling for him, and he finds it funny when someone complains his hair was constantly hitting them-

He also likes that ride that lifts the seats and spins, he loves it, despite being dizzy at the end of it

Tyler would go for the essentials first, like water bottles, veggies, eggs, etc. Then he gets the important cooking stuff, like meat (for his Pokemon), rice, bread and so on

Afterwards then he splurges on snacks--

Tyler once had Peanut butter Klawf sticks without knowing they were made from Klawf

He nearly puked on the first bite, then actually puked on the second, he can't look at Klawfs the same way-

Tyler loves the Summer, but if he's in need of a cool down, he'll just fly over to the nearest source of water, like a lake or beach and just hop right in

That or he'd get ice cream or sit in the shade while fanning his Dragonite, while she fans him with her wings

He'll use the AC in the Pokemon Center if nothing else works, but he doesn't like to loiter about

Tyler is the first one who enters the Haunted House-

He doesn't get scared of Ghost stories, in fact, it only excites him. So he'll be out trying to take pictures of a ghost and would scare others by telling stories he's heard. Plus since he can sorta see ghosts, he'd like to meet them more than anything

Though you can catch him off guard with a well placed jump scare

Tyler would be the kind of guy who would post pictures of the scenery he's in like some kind of blogger, and he would also post pictures of his battles, even his losses

Basically he's a mini Raihan

That's a tough one, but if I had to pick two songs, I say something high best like Sonic Frontiers' Undefeatable, and for the ending, something like The Case Study of Vanitas's season 1 ending