Quote Originally Posted by AnimeTheCat View Post
All of this crazy long post to ask. What do I do from here?! I've tried OOC from the very beginning. I've dropped items to slightly mitigate the strength penalty. I've coached and assist with spell selection. I have not, however, budged on a strong adherance to the rules, especially bonus stacking and skill use. How do I further help this player though? I can't just grant extra spells, especially temporary ones, because his character by it's nature of being a druid, will be more powerful than the other three (probably combined) and will overshadow them at everything if i'm not careful. I can't afford to give free handouts to a character that already has the potential to out-combat the entire rest of the party alone.

Any assistance the playground can provide would be appreciated. Ancedotes that are similar are encouraged. I really just don't know what to do from this point as I've exhausted every other idea I have.
Short version? Not your job.

You ask, "How do I help this player?" It sounds like you've done more than enough.

Seriously, it's like teaching a kid gratitude, here. Maybe he has it but refuses to show it. Maybe he doesn't have it. Maybe he'll have it later. Whatever the result, he's not grateful now, and there's very little you can do to force the issue.

You've done a lot for this player. But he simply wants. You give in on little things, he wants more. He wants to be able to steal with no skill check. He wants to just find loot because he asked. He wants to pick less-than-optimal spells he ends up blowing through, and gets frustrated when he does so. And yet, you keep accommodating him.

I'm not faulting you for that. Maybe I should, maybe I shouldn't, but I'm not. You're trying to make a positive experience for your player, and I can respect that.

But this is a player who will just keep wanting things, and not being grateful for what you've already done. And there's nothing more that you can really do, unless you're prepared to just give in on everything - a dangerous road to start down.

More importantly, however, is this - it's not your job. Your job, as DM, is to create a game world, to let the players have their fun in it, and to generally - generally, mind you - craft an experience that the players enjoy. This player, however, isn't asking for that - he's asking for specific benefits that his character hasn't earned, and that run afoul of the established rules. And it is not your job to provide that. Your job is to provide a positive experience for the table as a whole, not to yield to the demands of a single greedy player.

As such, you need to stop looking at this issue as "How do I help this player?" It's not your job to help him. It's your job to create a world in which he can find his own fun. Not to hand it to him on a silver platter.