If it really does turn out to be that way, again I'd do something just completely out there. Like vow to take revenge the next time something is stolen and completely disregard where the plot is taking you.
You're off to find so and so in this town and you come across a cave, explore teh cave and come back t ofind your stuff stolen. Again.
That's it, you proclaim, as you storm off in x random direction away from the town.
Perception check your way and hopefully find a track. Otherwise head back to the previous town and ask for the nearest bandit location. If none are found, backtrack more until you have nowhere left to backtrack.
Then just go North West.
Either the party will follow, and the DM will have to create a whole new theory of questing and structure, the DM will confess that he's been overabusive and "find" a way to get you your stuff back or know that it won't be stolen again, or.. it'll turn to OOC conversation and it will be discussed out.
The end answer is: Are you having fun? If you're not, the DM is not succeeding. And as such the whole group isn't. If you're the -only- one not having fun, well. That typically speaks volumes :( I'm afraid.
I know right? The details are great :) and the possibilities.. oh the story telling..
As a bard, this thread gives me the shivers and almost makes me want to skip the taverns in the evenings.
Why are there so many suggestions that have negative consequence? Some of these suggestions remind me of some Sunday morning cartoon villains, where say someone who has a really spectacular aptitude for climbing (+30 nearly always) goes to try and save a damsel tied to the edge of a cliff when a really short dastardly villain with a z-styled mustache steps out and says "myaaa, think you can just climb up and save her ey?" and then shoots a flaming arrow at the wall and sets the entire thing ablaze.
He probably comes with a dog that laughs afterwards.
I don't see why there's so much ... evil stored in the world. For those of you who are in the music world, at least from my experience it's not cut-throat when you're treating things as an enjoyable past time.
Here's what I see:
He's not demanding money, but takes it when offered
So as a DM, what are YOU trying to do with it?
Do you want to challenge him?
Then make it something of a story, The city can be inspired by both his generosity and skill that it builds an amphitheater of some sort and invites the bard, as an honored guest, to perform in a competition among some more recognized names. This gives you the opportunity to introduce legends (!) of lore, as well as invite nobility to properly see and contribute to the story and his fame. Add a prize, a worthy prize of a bard, to entice and reward good work. Add a villain if you like, but make this something that the rest of the party can see as bodyguards to help defend their team mate. That should show your team that they're willing to support your bard, and your bard see value in the team which I'm sure is there but recognizes that they support him for what he does, and who he is. This challenges his high score, but doesn't penalize him (he might lose the reward, but i'm sure you could twist it so that the reward is something off the high-end of the chart and if he loses (or someone steals the prize) the nobles and legends recognize him for all that he has done and give him (and the party) something for his and their talents.
Or he could turn it down. Who knows.
Do you want to reward him for using a skill he is proficient in?
I like the idea of an underling interested in becoming a student. This is just a treasure trove of story. The character already isn't asking for money, so he's not in it for wealth. Not to mention, you don't want people going over their global wealth or whatever it is. But a student, an underling, gives you potential to make his wealth of lore rather than of gold. This student, NOT interfering with his actual time and skills, could learn under him and bring a personal bond to a person and the place he is residing. Which opens up a whole realm of possibilities. Though to be honest now that I give it a good thought, I'm not sure how without causing mischief.
I also like the idea that other bards would speak of his name and his tales and his travels around other cities. Where they travel, at the very least he should be known.
What does he want?
Perhaps as a DM you ask him OOC if he wants something to be of his skill. If he literally tells you he's just rolling to roll, reward him by:
I'd rather get nothing than be penalized for using a skill.
Personally, and I could be (and hope to be) very wrong, but I feel it's the opposite. From what I've heard, everything post level 10 is pretty much large+, which means you're not only not able to trip/grapple/sunder/anything related to CMB, but you run the risk of being picked up by your head and tossed like a cabbage (Which almost happened on my very first combat round, but I dodged a bullet)
Sure, you can enlarge person or find some other means to be counted as a medium character, but those same means can usually be applied to the NPC which means that the issue is all the same.
There are strong halflings just like there are nimble paladins with the right feats
Not to mention everything is pretty much human sized. Walking into a tavern to play my flute is not only a difficulty, but a chore. I'm surprised climb checks aren't involved, and I tip my hat and coin to the man who created the halfling stairs.
And that's just to see what's on top of the table I try to play on.
Life in the short lane is rough. Sure, I can try to crawl into smaller holes to avoid potential death. But there's no benefit to it. I can (well my character can't but some can) haul 3x my own body weight, but I'm still light enough to be used in a cannon (if so enforced).
Life is rough, bein big pimpinnnnn