Man, I'm so glad I found this community! I don't know what I'd do with all these questions otherwise.
Anyway, as I mentioned earlier, this is my first time DMing. We managed to get the group mostly together after last session, so that's a bit less of a concern. Now I'm frustrated with one of my players trying to take advantage of me. He was the DM from last session, and has certainly played the most D&D of all of us, which makes this even more frustrating.
The first thing he asked was if he could start as a rich guy who's bored with life, instead of your stereotypical poor adventurer. He swore up and down it wouldn't affect gameplay, it was just a good background story. Foolishly, I agreed, and now he's saying things like "I buy this, I buy that, I invite all these obscenely important people over to my house," etc. Grrr. I'm thinking about having someone rob him so he's more on eqwual footing with everyone else.
Second, remember how two characters were going to try to rob his house? I asked him to give me an idea of what his house was like, and the sorts of defenses he might have. He asked if he coudl have magical defenses, and I said some, thinking of maybe a symbol of sleep and an alarm spell or something. No, he wants to have freaking Forbiddance cast on his bedroom, a statue to summon a cleric in case of trouble, oodles of guards, etc. adding up to like 10000GP, which he justifies by estimating his networth as being maybe 500000 GP or something. WTF? And he got annoyed that I added a door to the kitchen so his poor servants could escape in case of a fire. Fortunately, none of it really made a difference since the would-be thieves were real morons and were caught by a patrolling guard, but still.
Finally, last time I had an adventure in the sewers to get rid of the city's dire rat infestation. Naturally, being pompous and rich, he didn't go. Well, everyone levelled from the myriads of slain rodents, but he's like 1500XP away from level 4. Now he's whining about being far behind and wants to be rewarded for what he did last session - which was deciphering some poetry and selling all the crap he found from the first adventure. He claims he "didn't know" that he wouldn't get XP from that and would be so far behind. Huh? This is D&D, not Monopoly. So he wants me to catch him up to the rest of the group, and now he'd do more adventuring since "now he knows." WTF? Half a level of unearned XP? That's hardly fair to those who were getting grimy and diseased from fighting rats in the sewers. If I give it to him, it'll be a level in the NPC Aristocrat class.
I don't know, maybe I am overreacting a bit. But still, how do you deal with players who try to push your limits?