Yeah that is an interesting character, and I've never thought about that type before. That would be a fun character to write.
This brings Captain Jack Sparrow to mind. He's the MC, but he's only good for all the wrong reasons (greed and self-preservation). He's an absolute jerk, but is right most of the time.
Characters who are strategic. The reader shouldn't be asking, "Why is he doing X, when he could do Y? The character at some point needs to say, Lets do Y or We can't or won't do Y because.. The whole "Fly the eagles to Mt Doom" argument. Gandalf should have been on top of that and shut it down.
He did, Tolkien just got a reader-base who didn't read carefully Ironically, I'm not sure where I read that Gandalf explained this in-story, because now I can't find it.
I like to explain this from time to time. Tolkien likely intended for Frodo and Sam to die together on Mt. Doom, while confessing their forbidden love. Having the eagles rescue them from both these fates was probably a deus ex machina added by the publisher, who would have been concerned that the book was too dark.
I'm not a Muppet, I don't have a hole where you can- Actually, I just checked and there is a hole down there. I don't recommend trying to stick a hand in there though...
I always assumed that the reason for them sending in two inconspicuous Hobbits was because the only way to get there when Sauron was at full strength was to, simply, walk into Mordor. The difference between sending Clint Eastwood into the Soviet Union to steal the Firefox and trying to land a herd of C-130s full of Rangers and Marines to steal it. But anyway, I like my characters broken and on the edge of insanity. Cheradenine Zakalwe, who wakes up screaming and moves the chair out of every room he ever stays in. Bilbo Baggins, not in The Hobbit, but at the start of The Fellowship of the Ring, when he's always about one step away from just putting the Ring on and leaving it there. John Rambo in the book First Blood, who inadvertently lets the sheriff live because the sheriff is fleeing in blind panic, while Rambo is moving carefully, looking for the ambushes and booby traps he assumes are waiting for him.
As for the Eagles, the sky is low and choked with smoke and ash in Mordor. The only reason they could fly to pick up Frodo and Sam was that Mordor had been emptied for the war at the gates; Frodo and Sam were only able to make it to Mt Doom because Sauron had most of his troops heading for Gondor because he thought that the ring was going to Minas Tireth. If the eagles had flown the ring to Mt Doom without all this other stuff happening, they wouldn't have got more than a mile into Mordor before getting shot down and basically handing the ring over on a platter. As for characters, I like sincere, sturdy everymen. Like Sam, come to think of it.
