Who Needs Friends When You Have Dragons?

This oneshot is a practice run for myself, to figure out how to write them in the first place. It's not terribly complete, but it is a thing. Based on a group of characters from a short story I wrote. See the story summary here. Set in a rather goofy world where being a hero or a villain is a literal job title.
I'll take any advice or thoughts people have for me, but please consider that I'm a newbie at this and be kind. (Also I ran out of time and brainpower to finish this during the challenge proper but I wanted to post something while people were still looking so I could hopefully get some advice.) Overall I'm proud that I tried, and I do want to try again.

Quick Summary

The characters are a group of hero friends who occasionally work together to do the things that heroes do. On this particular occasion, they have previously enraged a dragon that is now rampaging over the countryside. They must find the dragon, and a way to stop it, before their frenemy Roble O'Grady swoops in to take all the glory and make them look like idiots.

Structure

Exposition

The one shot opens with the group waking up at their campsite (minus Uvdalf if he's being played by a player). Each player should have picked one of the characters to play, and then privately chosen one of 3 starting quests.

• Go to the Pyres of Amorgan to enchant their weapons
• Hunt a chimera
• Get the local lord off their back by doing a delivery for his mother-in-law

It's a chance for the group to establish characters and dynamics. Discuss, introduce each other, possibly even get into fights with each other. This is the place for the GM to let them get going. Keep it quick, though, especially if Uvdalf is a PC. Set a literal timer. Like 5-10 minutes, depending on how well the players already know each other. These guys in-game already know each other, so this is just to let the players explore their characters and role-play a little.
The GM should take a few moments to provide little "reminders" as to "the thing that happened yesterday that we shall not speak of."
When they've finally decided which one they're actually going to do, Uvdalf shows up, in a panic.

Conflict

Uvdalf, as is typical for him, has screwed something up. At least this time it's not just his fault.
The day before, the lot of them attacked an evil overlord and just barely managed to defeat them. (See Overlords for a few possibilities of who they defeated). Somehow, during the course of the battle, a dragon was set loose and is now rampaging across the countryside. Depending on who is in the party, different things would have happened to ensure that they are all responsible for this disaster in some way, because they have offended the dragon.

• Thezzag stole her egg for use in a culinary creation
• Uvdalf hit the dragon with a spell that made it larger (and thus a harder fight for a larger party of PCs)
• Zachonicon broke the chains holding the dragon
• Jehoram stabbed it, but only a little prickle so enough to make it mad but not enough to slow it down
• Kimna used it to climb up on a wall and its dignity is offended

Suggested way of relaying these details is that the GM narrates short little flashbacks, possibly with rolls involved to see how bad it got and thus which one of them the dragon will hate more.
What the hook boils down to is that "it's all y'all's fault, so now we need to go clean up this mess." To add a bit more of a ticking clock to it, state that the famous Hero Roble O'Grady is in the area and he will handle it for them if they don't move it, and that would just be embarrassing since he's kind of a credit-stealing jerk who would take the chance to take away a lot of the influence they've made in the area.
This would be a point to introduce some form of the idea of a Coolness Meter. Being a hero is a job, and with it comes certain expectations. The more ostentatious the actions of the party, the more of these "points" they should get, because by the time we get to the end of the adventure how much of a reward they'll get will depend on how cool the people they've saved think they are.

Rising Action

Event #1

The party goes to a town that was attacked by the dragon to figure out where it went and how to defeat it. The encounters here can go several ways. They can choose to fight for the information, bargain, help clean up the town, however it goes.
There are three crucial points that the party needs to learn before they can move on. Whether someone lets it slip, or shouts it at them as they're tossed out of town, they need to somehow uncover the following facts.

1. The dragon is stronger than they thought, as evidenced by the fact that the last time they fought the dragon it did not go down so easily. Therefore, to bring it down for good or even just drive it off effectively, they will need to make a special weapon of some kind. (The GM should choose what this weapon might be.)
2. The dragon is going to attack a particular city because that is where this dragon believes the heroes that offended it to be. This attack will come soon, so the party can't lollygag and gallivant around. (GM to set a time table that leaves a reasonable in-game amount of time for collecting the weapon and then traveling to the city without much extra time.)
3. Roble O'Grady has an in with the mayor of the city, so if the heroes don't do a great job then he'll get the credit. Also if they take too long then he'll get there first and that will make it even harder to fight the dragon. If they really investigate this guy, one idea is to provide tips and tricks as to his weaknesses.

With this information in hand, the players should be strongly encouraged to get going on crafting that weapon.
The coolness meter should be tallied here. Small effects, to maybe show up a local bully, or see what happens when a hero doesn't have so much fame to their name.
I would suggest that, while not directly related to being cool, the villagers would be more likely to provide some kind of bonus aid in the future dragon battle if the party aren't complete jerks to them.

Event #2

There are a number of different ways that the item hunt could go. There are poisons that need a particular flower, a knife that will need a special kind of ore to be crafted, perhaps some ancient gemstone lost to the dungeons over there. Just a quick little fetch quest to grant a fight or a little bit of an investigation and use slightly different skills.
Once the players have the item, they need to go see the witch. Use whatever aesthetic is wanted. In this world, witches are more like highly specialized pharmacists who are supposed to have a particular look. If there's enough time or the resource gathering didn't take long, she can fight them or otherwise challenge the party before she crafts what they need.
If they don't manage to get the item or craft the weapon, just put them at a disadvantage in the fight ahead. It's harder to look cool if you can't actually kill the thing, but it should still be possible. These guys are professionals, after all.
Witches do not care about coolness, so any part of the meter tallied here can be credited to them practicing their craft, warming up for the big event, or something like that.

Climax

The dragon is going to the walls of the local city. This is obvious, and as such Roble O'Grady could arrive at any minute. The job of the party is to stop the dragon by whatever means they choose, and to do so before it does a lot of damage to the city, before Roble O'Grady arrives and swoops in to take the kill, or before one of the party gets killed.
The dragon can arrive before the party, as they arrive, or the GM can give the players a few turns to prep their defenses and plan their attack. Up to them, and how they feel the party has done at keeping things moving (reward moving quickly, give floundering players a chance to figure things out, or throw people into a fight to keep it interesting, whatever works).
The dragon is a big sucker that will be hard to damage without the appropriate weapon (and feel free to let the players squabble over who gets to use the weapon). It should do a lot of damage if it hits, but it should have a difficult time hitting the players. In short, as long as they keep on top of it, it should be fairly simple for them to stay alive. Also, the villagers should get behind the walls quickly so there's less danger for them.
GM's discretion as to when Roble O'Grady shows up. Because he will show up, with a varying number of companions depending on how challenging the fight should be. He's going to try to take down the dragon and look cool doing it. The players are now trying to stop the dragon while making it clear that they are the ones doing so, and that they are suitably epic or else why are they even professional heroes?
Remember the coolness meter! This is where it comes into play the most. It's not a victory condition so much as it affects the reward at the end. Also a way to reward players for showing off and doing ridiculous and impressive things. Note that Roble does not have the special weapon to defeat the dragon, so if he wants to do the final takedown he'll probably be trying to take it away from the PCs.
Victory is achieved when the dragon is driven off (killed, talked down, gets a call from his mother-in-law and has to bail, etc). This can be a good moment for a quick conversation with Roble, to really drive home the fact that he's the actual antagonist of the story.

Resolution

Depending on how the players did, the townsfolk can be very impressed with them and reward them mightily, or they can snub them and give all the credit to Roble O'Grady and call them sidekicks. If they did especially poorly at public relations, they can even get run off in disgrace.
Best case scenario might include some kind of parade and lots of rewards.
Worst case is that they end up back at the campsite where they started, slightly singed, but at least the dragon didn't eat anyone.

Relations

Protagonists

This one-shot has an existing squad of characters. They can be employed in any configuration, since they're meant to be a loose group of friends and Heroes who occasionally work together. The general dynamic is that they're all friends, but they're a mix of strong personalities.

• Jehoram: a prince who defied his parents' wishes and became a Hero to do something with his life before he had to settle down and take the throne. Despite this moment of rebellion, he's a pretty standard lawful good fighter, from a country that uses magic. Generally defaults to be the leader of the group because he's the only one who doesn't have any outstanding warrants so it's just easier if he takes the lead whenever they have to be civilized. Kind of a doofus when it comes to love and romance.
• Zachonicon: cyborg warrior, he's the easy-going peacemaker of the group. Sort of. When he's not joking around and riling them up by accident. He's a tank kind of character. Sensible. Vulnerable to diseases, but has the most common sense of anyone in the group.
• Kimna: a very sneaky thief. Has the most warrants out of anyone in the party. If someone asks, you haven't seen her lately. Dislikes squirrels and other small animals. Can probably be found up a tree lurking in the shadows. At her best when working with or talking with her friends one-on-one. In the group as a whole, she tends to push a lot of buttons. The only girl of the group, and she's not there for the romance so don't ask her if she's hooking up with her friends.
• Thezzag: a very traditional dwarf with an axe and a tendency towards mining. Best cook and scout of the group. Ranger type character. Acts grumpy but he really isn't. Loves his grandma very much.

Those are the four mains. The next character is one who can be used by a player if five slots are needed, and otherwise can be an NPC companion used by the GM.

• Uvdalf the Uncorruptible: wizard who is average in intelligence stat, fairly high in power, but low in wisdom. Makes bad decisions. Least liked of the whole group. Has enough power to accomplish a lot but usually just ends up making more problems. Trying his best, but his arrogance keeps getting in the way. He's the instigator of the main plot of the one-shot.

Competitors

Roble O'Grady is not the greatest hero ever, but he is good at stealing credit. Comes with a small band of rough equivalents to the party, so that he can fight the dragon in the last battle.

Backdrops

Locations

There is a handful of locations that the GM should prepare in advance for this to run smoothly.

1. The campsite. Starting zone, a basic layout and background.
2. The village. The first zone they investigate. This will need NPCs to populate, clues to find, and points where the dragon caused damage.
3. The road to the ultimate weapon. This one will depend on what you want the weapon to be. It could be a special poison, a rare type of ore, an ancient artifact, etc. Depending on what it is, the necessary backdrop for getting it will change.
4. The witch's cottage. This is a crazy world, so do what you want with the aesthetic. Go full cliche, go anachronistic, something bright and cheerful, whatever you want. There just needs to be a powerful magic-user for hire who can put the weapon together for them.
5. The area just outside the city. For the final battle. Will need enough space for a dragon to move around, and for two groups of fighters to attack.
6. Bonus ceremonial area. For the end, for the recognition after the fight, if the GM wants to change location and do something fancy. I dunno.