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[Scoops Novel]

LEVEL 1

[EuchreJack]

*EuchreJack Slays Novel*
*EuchreJack Levels up to 20*

[EuchreJack]

I win!

However, although I doubt anyone will objectively beat my record, the subjective nature of the task means that others could join me in Level 20.
We could form a Guild or Adventuring Team!

[Scoops Novel]

*Ahem*

My results from my own meticulous study.

Level 1: Somewhat Giant Dragonborn who has his source of power in the village tries to take it over.

Too much exposition, I'll admit.

2: Banish the Poltergeist

Level 3: 3 adventures

-   Identify the person trying to murder you at a event/place you're attending with a lot of suspects.
-   The Mummy of the Week - Meaty but manageable antagonist
-   Some weird shit, to really give that adventuring feel

Level 4:

Something Dramatic, which provides for backstories. One big adventure to really give the feel you're players in the world now.

Level 5:

Something scarier - say a follow-up like The Mummy's Maker – which has the feeling of breadth of a big Call of Cthulu adventure. It can be made as long or short as it needs to be to be satisfying.

Level 6:

Has to feel like a bump up. I think it should be more then one adventure.

Level 7:

You're professional. Proficient. Feel it. A adventure which doesn't cooperate at all, plot-wise, gameplay-wise, but which still works because you're that good - that's what you want here.

Something like a mystery that doesn’t flow. Where the players provide the Oomph.

That's about as far as I've gotten.

[EuchreJack]

*EuchreJack, Level 20 Paladin offers to train Novel-Prime in an epic training montage.*

[Scoops Novel]

Ah, i see you slew my nemesis Novel Subprime Mortgage and Mortgage Accessories.

[EuchreJack]

Ah, i see you slew my nemesis Novel Subprime Mortgage and Mortgage Accessories.

Yes, and now prepare for a training montage where you learn basic home repair and budgeting!

[Scoops Novel]

Level 6:

Has to feel like a bump up. I think it should be more then one adventure.

This is actually kinda hard to do. You customarily tackle such big concepts at the levels preceding this it's challenging to do something that doesn't seem like more of the same or just overkill.

[EuchreJack]

Level 6:

Has to feel like a bump up. I think it should be more then one adventure.

This is actually kinda hard to do. You customarily tackle such big concepts at the levels preceding this it's challenging to do something that doesn't seem like more of the same or just overkill.

You can change the scale.  Instead of a monster terrorizing a village, upgrade to a monster terrorizing a kingdom.  Cheap but effective.
In addition or alternatively, you could tackle a new mechanic. 
For example, fighting the monster terrorizing a village is easy since you'll probably bump into it.
Fighting a monster terrorizing a kingdom requires navigating the kingdom, inquiring about clues, tracking the monster, and maybe even outguessing the monster's next target.

[Scoops Novel]

Ok, that's the first adventure for level 6. I feel there should be at least 2.

Surprise: there's a monster RULING the kingdom!

[Scoops Novel]

One more thing; I feel at level 8 you've got to give them some bigger motivation. No character actually wants to level up to 20, and it would be boring if they did. They need a more short-term goal befitting of superhuman adventurers.

[EuchreJack]

At level 20, you're in charge of everything. It sucks.

Level 8 is not Superhuman.  Hell, I'm a Level 20, and I'm still ordinary human.

At some point, levelling up comes down to "Sigh, somebody has to do it..."

[Scoops Novel]

In-verse you're a journeyman adventurer, taking on threats to the kingdom...

Your basically a special agent. What do special agents want? A exit strategy and a comfortable retirement.

You should basically have a plot line where you're trying to relax without attracting random people who want to kill you for the glory, revenge or goods... like you have so many others.

You're building your dungeon...

[EuchreJack]

Hm, consider Marshall Dillon from the TV western Gunsmoke (or Gunkill, as I jokingly refer to its summary justice in many cases).

He's a Level 20 Lawman.  He defeats every foe.  One could argue that Dodge is his Dungeon, as the bad guys that enter there tend to either die there or get run off with nothing.  His keys to success are that is he just better than most everybody else, and he has friends to help him.  The community alternates between assisting and hindering him (comparing them to the walls of the dungeon would be appropriate).  I suspect one reason Dodge grows in all those years is that Marshall Dillon settles all the good people there.