As a little background, in case it matters: most of the players in my group (but not all) are college aged, and all of them are personal friends of mine. We're playing D&D 3.5. I myself am the group's only real DM, but even I'm more of a long-time listener than a long-time caller. I've been running roleplaying games for most of my life, but I've probably only run half a dozen real play sessions of any system as complex as D&D.
My group isn't currently playing because we're separated for work reasons. This gives me a little time to reflect before jumping back in.
So my players — let me tell you 'bout my players.
The Barbarian loves D&D perhaps more than anyone else at the table. But he couldn't tell you just what a saving throw is. He tries, but he's got mild dyslexia, and hates reading almost as much as he loves role-playing. So he tries to rely on me/other players for the rules and plays a Barbarian because 'hit it with my axe' is always the correct solution. He's never once invoked his Barbarian Rage power.
The Wizard is stunningly poor at thinking strategically. I have to practically bean him over the head out-of-character to remind him that he has the power to cast magic spells. In addition, he's so shy and non-confrontational that he can't even hold an assertive conversation with fictional NPCs.
The Bard is super chill. No matter what happens, he's happy, because I gave him 500 bonus XP at the start of the campaign for drawing a picture of his character. And for pretending that all the other PC's are members of his delusional band. No problems here.
The Rogue is the only player who I could say with confidence has read the rulebook. Many times, he's snuck off in the middle of the night to go use his Sneak skill, and the entire table (myself very nearly included) has sat in awe as he uses sheer brainpower to accomplish things the other party members never thought possible. There's no Munchkin roleplaying here, no Thespian roleplaying--just pure creative problem-solving.
The Ranger (and elf Ranger, no less) doesn't seem to have grasped the ways in which D&D is different from a video game. He's a little frustrated because his character doesn't deal much damage with a default shortbow, but can't seem to make the leap to realizing that he needs to take some initiative if he wants to change that. I can't even get the guy to go shopping for a composite longbow.
So those are the regulars.
My question here isn't about the fact that most of them don't know the rules very well; I've more or less given up on forcing them to put in study time they don't want to, and instead choose to hope that over time, with gentle reminders, they'll pick up the rules they want to pick up and become pretty competent. This seems to have started working, to a degree.
My Problem Is:
How do I keep the game entertaining for this entire band of misfits at once? The Rogue is getting a little bored because no one else can keep up with him. He's asking me about a Ninja prestige class while I still have to walk some of the other players through leveling up their base class. The Wizard is getting a little discouraged because he can't keep up with the others. The Barbarian's fun times are interrupted every once in a while when he realizes that he could be doing things even cooler than hitting if he'd read a few more rules. The Ranger is just getting aggravated that his Ranger isn't a badass yet, and he's already level 3.
Over the last couple sessions, I once let the Wizard try his hand at being the DM. To make a long and depressingly bizarre story short, the party is scattered across half the fictional continent, and the party members who aren't in captivity are more interested in getting back 20K of 'Russian' gold than rescuing the others. I'm uncertain of my ability to bring everyone back onto the rails, because even getting them to finish a single dungeon is a major accomplishment. Even if I give them a map, they manage to get lost and conclude that they're supposed to exit through the nearest window.
You're free to tell me that we're playing this game wrong in every conceivable way. But please try to include an answer to the question as well if you choose to respond.