DND (5E): Monthly One-Shot: Adventures from a Hat

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Hey guys!
It's time again for another one-shot game in our monthly series.

This time, we're doing something a bit different.

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Story:
A ruler of a faraway kingdom has been kidnapped, and is being held captive by a terrible monster at the highest point of a castle tower.
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Well, that's the story. Seem a bit too unspecific though, right? Well, that's where the players help the DM out in this game of "Adventures from a Hat".

It's a gametype I made up based on the gameshow "Whose Line is it Anyway", where basically before the game starts, I have players write suggestions on slips of paper for things like "NPC to run into", "Monster who would fight the heroes", or "Trap for heroes to overcome". And basically, as the campaign is going and the time arises for a suggestion, I'll pull one from the Hat of Adventure and improv it into the story.

It's been years since I've run a game like this, but it's always been a lot of fun, and I've grown a lot in experience as a DM since my last one, so this should be even better than ever before!
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Since this is a one-shot, we aren't going to be worrying about XP since it won't carry over.
I would like for players to bring level 5 characters that were created using OFFICIAL Wizards of the Coast 5th Edition material, such as the Player's Handbook.

There is actually one one restriction on class/race/spells/etc, and that is flying. Please don't bring a character who can fly via normal means like wings, or use of the fly spell. If your character can just fly up the side of the castle, the whole campaign becomes kind of pointless.

Otherwise, there are no other restrictions.

When giving your character gold and equipment, I will ask that you follow the player's handbook's guide on what your class and background allow you to start with.
In addition, as a bonus to spice things up, everyone is allowed to choose one UNCOMMON magic item to have their character start with. The list of magic items you can choose from can be found in the Dungeon Master's guide.
Also, for assigning points to attributes, please start with the 27 point-by system. This helps me make sure everyone is playing fairly.

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ALSO, please be sure to have $5 ready to pay the store.

Thanks guys, looking forward to seeing everyone!
-Doug