Some of the more entertaining ideas floating around about Will, and my quick-n-dirty responses (as I am at work);
1. He's a pansy. Ah, no. Sorry. Nobody avoids drowning that many times just to be called a wimp. Physically, he's been through almost as much as Jack in this series thus far, and while many of us might call Jack's walk "sissy," there's few if any who would refer to he himself as that way.
2. Life as his wife would be oppressive and traditional. Again, where does THIS come from? Certainly not canon. I don't know of many 18th-century suitors who taught their highborn girlfriends all their fencing moves, or expect a society lady to know how to shoot a rifle or hold her own in a physical altercation. If anything, Will's both young enough to grow old with (not being 20 years older, he won't kick off first, as men are wont to do even at the same age) and to be flexible for making up their own unusual lifestyle.
3. Will's an asshole because he tricked Jack and lied in the first movie. Yes, because Will's certainly alone in THIS respect. Everyone else is pure as snow. LOL. All I can remember him doing along these lines is knocking Jack in the head with an oar, after the man refused to give him a direct answer regarding saving a woman's life AND had spent their entire time together plotting to use Will as leverage for his own ends without admitting or explaining this sufficiently to Will, and without Will's consent (from Will's POV). If Will had done nothing else ever for Jack, he broke him out of jail and helped him sail out of Port Royal; Jack could've knocked him in the head and dumped him in the ocean after that point. Maybe if Will had kissed Jack before he knocked him in the head, that would make people feel better? Would me. *G*
4. The Holy Duality, Part Un: Will's an asshole and a pansy ... but he's unselfish and noble enough to give up the woman he loves for his chief rival to move right in. ROFL! Delusional, much? Either he's a jerk or he's not. Decide.
5. The Holy Duality, Part Deux: It's wrong to say Jack would never settle down with a woman, because he's human and needs love! ... but Will ought to be content sailing around for 900 years without a romantic partner, escorting sailors to their deaths. Was Will outfitted with robot parts when I wasn't looking? When did POTC turn into A.I.? (Then again, as long as THAT movie was, there might've been a hidden POTC plot somewhere in there.) Again, either you admit Jack and Will are both human with needs (as human as a movie character can get, that is), or neither of them are.
Hey, I'm a Will community moderator. This sort of thing is in my job description. *G*