Okay, I think I need to explain a few things, as well as tell you guys where I'm going with this before we proceed any further.
First off: Yes Arillious, dressing up like Legion Soldiers and killing a bunch of Stormcloaks while spitting in Ulfric's face would be really stupid if the rebellion is 8 people. However, we're not the only part of the rebellion. As I've said before, Simus commands about a third of Skyrim's armies and they're all loyal to him. That means he's got other groups in other camps doing other things to make a large scale rebellion happen. We're only one "cell" of that. The other "cells" don't know what each other are doing so if they're compromised, they can't compromise anyone else because they don't know they exist. We're the "loud cell", the special ops group that does the most damage. If Ulfric thinks it's just us, he's going to focus only on us and that gives everyone else time to do their jobs (Vignar's taking care of all that behind the scenes. That's one reason both he and Simus are leading the rebellion.)
Also, Ulfric doesn't know Simus is leading the rebellion and still believes Simus is preparing a third of Skyrim's armies to figh the Dominion. Considering Ulfric has to go through the Empire to get to the Dominon and the Empire won't just allow Ulfric to do that, it's a good idea for the Stormcloaks to be familliar with Legion equipment. What it can do, what it can't, its strengths, its weaknesses, that sort of thing. So if he sees guys in Legion gear in Simus' sphere of influence, it wouldn't look all that strange. Plus, there are probably hundreds of Stormcloaks with pilfered legion gear since it's better than Stormcloak gear. Just like U.S troops in Vietnam using AK-47's because back then M16's were prone to jamming and AK-47's almost never did.
Also, you guys are NOT going to spend the rest of the RP in Legion gear unless you want to. The point of using it is to
A: Give everyone a standard equipment base that almost everyone in Tamriel is familiar with and
B: See what you guys can do with basic, unenchanted gear that you're not used to working with. That puts you out of your comfort zone, and if you're all uncomfortable than you all work together more readily. Even Simus and Alice have basic gear (I changed my last post to make it basic.) for the above reasons. Plus, Alice doesn't want or deserve special treatment and Simus wants to set a good example for the rest of you, considering he's leading you guys and he needs you to trust him.
So Arctic, your guess at what I was doing was correct. At the end of training, Simus will give you guys your weapons back and ask (not order) you guys to keep the armor as a reminder of what you've accomplished together.
Also Arillious, no, under normal circumstances the Emprie would absolutly not tolerate an overt traitor like Simus to create his own legion. It has more than enough manpower to replace its lost legion in Skyrim. However, the politilcal situation between them and the Dominion has gotten so bad that they need every man they can get on the front line. Skyrim comming back into the fold would be really nice, but they're not going to waste more men trying to get it back. Simus however is providing an oppertunity to return Skyrim at no cost to the Empire. World powers always take advantage of people fighting for territory in their name so they don't have to. They're going to let Simus do his thing because it's convenient and if he wins, they get Skrim back, which opens a huge pool of manpower for them, not to mention a very experienced general they can let lose on the Dominon.
And sorry about that Meben. I'll take your suggestion and edit my post. I was trying to think of a way to convince Raylen to stay while staying in character and I fell a little short.
Thank you all for bringing this to my attention: I want this to be a good, long-lived RP and I need your input to do that. I hope I cleard some things up, but please let me know if I further obfuscated anything.