You know, all your recent talk about archetypes reminds me that I still think you should give Inu x Boku SS another go, despite the fact that it's essentially a butler comedy:
-Ririchiyo means the show is essentially the closest thing we'll get to a Kuroneko POV anime, until someone decides to adapt the Ore wa Kouhai spinoff manga.
-Remember how Hyouka gives Chitanda some significant character development in the final scene but you probably felt it was too little, too late? InuBoku does something similar with Soushi, except just a tad earlier in the story and with much greater significance.
-Master Troll is awesome.
-Building on the previous point, I feel like it has the kind of things you're M for in spades.
(I know I've also mentioned it before, but Otome Youkai Zakuro is also a nicely irony tinged bit of josei-infused seinen - bishie military dude who is secretly terrified of spirits gets partnered with tempermental kitsune girl.)
So I guess the big question I need to decide is whether to try and scrounge up a fifth player for our LAN group or just decide that failing can't be too embarassing when there's only one stranger present.
There are a few potential candidates, including one of my close anime buddies - the only problem being that the main way I can think of interesting him in the game is what kicked off my interest in the game. AKA mai waifu (we have similar, er, tastes).
(One thing that does help here is the low system requirements. With a lot of games, I have to get anyone attending to lug over a desktop. On the other hand, once my dad and I get our HTPC up and running again, we'll have more computer capable of running LoL than family members. Not even joking.)
Play Co-op 5v5 against bots. You still earn IP and gain levels in which the cap is 30(IP is used to purchase champions and runes if you don't want to spend money via RP). There's also tutorials to get your friends to understand mechanics and objectives. The shop menu also highlights recommended items and there's champions that have recommended tags which make it easier. Also the free to play champion pool (they change every week, then you a new bunch is the following week. They also don't require IP or RP to purchase them).
LoL is a great game because it's very easy to learn and pick up, but an infinite skill cap particularly when you start doing ranked 5v5 ques where it's all about teamwork. It's the most popular e-sport for a season and it's rapidly growing. It's by far already exceeded Starcraft:Brood War status just in Korea alone, but unlike that game LoL is truly global. There's nothing to be afraid of. It's not like DOTA/DOTA2 where it's pretty much hell for newbies and there isn't much of a tutorial.
As for Uchouten, it's not just crossdressing but gendershifting. I actually lold.
As you may or may not be aware, I rarely play multiplayer outside of LAN parties due to time constraints. If I try the game, it's most likely going to be within a LAN party setting.
How well is the game going to work if my regular LAN group consists of four guys with no MOBA experience? Also, is it going to be a big issue if some players have time to play outside of the LAN and some don't? (namely: some players will probably have more experience than others.)
P.S. Not sure if you noticed, but Uchouten Kazoku has crossdressing despite Okada not being involved.