I keep wondering about so many little things.
 
This holds true in both real life and when playing an online game with others. In life you can be scared or feel uneasy when you do something, afraid it might be the wrong way to do it or not as fluid as others might have handled the same thing. In games you can be scared or feel uneasy when you play certain classes/specializations or wield specific weapons. You might still get the job done but not as fluid as another class/weapon might have and another class/weapon might have done it better or faster.

That feeling sucks balls. Especially in RPG's, MMO's and shooters it can be painfully obvious how accepted a class or weapon is compared to others due to the feedback. My standard Halo weapons often include the Assault Rifle and DMR/Pistol. Some people flip the hell out of seeing me wield a AR because they're afraid it doesn't hold up against a DMR. It does, barely, and it's just my style of play (and it has served me more than well). Shooters, especially the unorganized death match kind, can be very lone wolf mode however and it is in MMO's we find the best examples of the social acceptance of weapons/classes. I understand the frustration that comes from one member dragging the group down with a gimped play style but there are a lot of options nowadays to prevent such things from happening. Don't want to talk about that though, my point here is that people can feel very judged (and eventually kicked from groups) or bad about themselves because the fact is they're dragging their groups down or they make their fellow players skittish about their survival chances. 
 
The good news is a lot of games offer balanced options regarding play styles and games like Guild Wars 2 plainly restrict weapon types to certain classes. Even better when a Warrior or Thief equips a Rifle or Bow and suddenly finds a new set of ranged skills on the action bar. No blocked skills because you're wielding the wrong weapon, no gimped damage output because you're supposed to be a melee class instead of a ranged one. There's still a bit of bias towards certain weapons (A melee Ranger with a greatsword should probably not be in the thick of the battle when the boss goes into overdrive, nor should a Elementalist try to take hits from a strong enemy wielding just two daggers) but it certainly allows for more freedom between classes and their play styles. And luckily the acceptance of that play style by others. Guild Wars 2 succeeds in places other team based games often fail simply because it allows people to feel strong and useful despite what their player character is build for. Sure the mechanics in the game could easily be called zerging but the game breaks a lot of the old grouping boundaries while still giving you the feeling you're part of a group. And not being punished for it because every crafting node, experience point or item drop is shared between participating players. 
 
I stand and watch, I see a player wielding a Plasma Pistol and he's positively beating the shit out of people who stick to their Shotgun. I see a Ranger charge at me with a Greatsword and knock me silly. I see freedom and fun, endorsed by developers and players alike. It's time weapon/class/spec became a strategic element in games which forces us to think on our feet and adapt to our enemies style.

I am aware there are games out there which already do this and I applaud those efforts. It adds to the immersion and it allows players to follow their fantasy instead of being forced into certain options to get the max out of their class/race/etc (and who doesn't want to win, right?).
 
Feel free to share any crazy class/weapon/anything combo's you made work in games, I'm sure there's a good story in it!

Well that sounds great that players can play how they want to play and not feel like they're being punished for deviating from, or forced into adhering to, the established archetypes, but also sounds like further proof that I should continue not playing MMO's. And multiplayer games in general. I don't want anyone telling me how I should or shouldn't play something, I'll play how I want to, damn it! If I do suck playing more like everybody else won't help me do any better, of that I can assure you!

That being said I seem to stick to typical setups for these things. Or at least I'm having a hard time thinking of a real radical set up I ever rocked.

Back when I was playing Call of Duty 4 or MW2 I'd play as a somewhat stealth focused light machine gunner, which is possibly sort of odd, but don't really have any good stories about it.

I feel like playing some Guild Wars 2 now. GS ranger and dagger ele may not be that effective in dungeons, but there's half a goddamn world in that game to run around seriously wreck face.

@TaliciaDragonsong: That's true, but I usually save the experimenting for a half hour or so of fucking around after I've finished the game already. I guess I'm just boring that way. It's partially because I fear getting to a point where I'm stuck because I wasn't using the thing you were supposed to be using and now I have to give up or start over. Although I suppose that predicament is quite rare these days, what with all most developers bending over backwards to make sure everybody can finish their games no matter what.

In theory, I endorse this idea fully. But after playing hundreds of multiplayer games, I've kind of come to a painfully obvious conclusion here:

These things are really, really hard to balance properly. In many cases, you just can't balance all possible combinations... in fact, for many games, finding the best combinations of units, weapons, skills or whatever IS the game. The "different but equal" approach to Starcraft eventually became pretty successful but only after a lot of patches and heavy exploration of the meta game of finding effective combinations.

So many games tried to follow this model and failed to build a thriving balance out of it. Invariably a simpler way to create fairness is to make everything very similar. Put simply, regardless of what you pick, you'll have at least a reasonable, baseline chance of succeeding that's within player tolerance. Some people would say this makes a game less interesting (that's debatable). As a contemporary example, there are a lot of guns in Battlefield 3. However, because most weapons within any given type are so similar, the gap between "best" and "worst" is small enough for nobody but the most hardcore care. Quite frankly, those people will never be pleased, no matter how much or how little you nerf the M16.

The absolute worst is in the MOBA genre, notably League of Legends, where more times than I can count unorthodox builds are publicly chastised (often with extremely harsh language). This is in a genre where you need to communicate, and simply can't ignore your team. This isn't totally unjustified; if you do poorly in such a game, you can ruin the experience of 4 other players while wasting twenty minutes - or more - of their time. Still, how is any of that in the spirit of the game? How do you fix the problem there? Is this even a problem at all?

I think the nature of "optimal" builds and choices has pushed me away from a lot of strategy games, Diablo, and LoL. It was fun from the 90's and 2000's but trying to find these things, or just googling them, has lost its charm. I play a warrior in GW2, predominately using a sword and shield, and I feel they did a great job straddling the difference there between PvE and PvP customization.