Yeah, Omega is a great time to level because of how high the XP bonus gets by the end. Also, in case you didn't already know, you can use the Cube Shards you get from Terminals to buy Fortune Cards. You'll mostly get boosts from the cards, so you shouldn't have any problem keeping yourself stocked up on boosts.
Leveling Cyclops is a decent idea since he will give all your other characters a 10% XP bonus. Plus, he's really simple to level. Just max out Master Tactician and Channeled Blast then spin in circles and you'll have no problem with most content.
If you want to get the most out of everything you listed, I'd suggest waiting until Monday if you have time to play then. Every Monday special boxes drop from the bosses in Midtown. The XP from the boxes will be boosted, your Patrol Boosts will be useful, and each boss will have a chance to activate the Odin's Bounty boost. Also if you have the credits, you can reroll your LQs so those are in Midtown too and get bonus from that as well.
One of my favorite WW2 games is The Saboteur. It's a bit different than most games set during that time since it's a GTA style game rather than an FPS. It's really fun and the visual aesthetics are really nice.
The Sniper Elite series is really good too if you like a slower and more methodical style shooter. Plus, Sniper Elite 3 is one of the only games that takes place in the African front during WW2.
If you plan on heading down the West coast, I'd definitely recommend Crater Lake in Oregon, Mount St Helens in Washington, and the Grand Canyon in Arizona. They all look nice in pictures, but seeing them in person is very different. I'm not sure if all of them are open during the winter though.
There's also the Experience Music Project and Pike Place Market in Seattle. Both are kind of touristy, but still worth checking out at least once. Besides music stuff, I think there are video game and Star Wars exhibits going on in the EMP right now if you're into either of those.
A lot of good ones have already been suggested. I also like Aura - Maryuuinkouga Saigo no Tatakai (The Final Battle of Maryuin Koga). It's pretty depressing though, so I wouldn't watch it unless you're in the mood for something like that.
I saw that Manga promo so many times as a kid that the KMFDM song is permanently burned into my memory. Glad to see you're planning on watching Kino's Journey. It's my favorite show. It's slow and simple but thought-provoking at times. The rabbit episode (episode 2) is a perfect example of that.
I always liked Sis from Alpha Protocol. She's very tough and dangerous, but there is also a vulnerability to her. Plus some of the missions involving her are some of my favorite in the game. I wish the game gave more information about her and her background.