Character Advancement

A Swashbuckling Campaign


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The majority of level advancement in this campain will be handled through a “Keystone” leveling system; I sourced the name, idea, and broad mechanics from this youtube video released on the Mystic Arts youtube channel. This system is intended to combine the strengths of both XP and Milestone leveling, particularly in the context of a lightly-guided sandbox campaign structure, while avoiding some of their pitfalls. Keystones should motivate players to advance their characters by engaging with the setting.

As the party completes quests, attains notable accomplishments, collects bounties, and amasses treasure, they will gain Keystones. These differ from XP in that they are solely assigned by the DM on a case by case basis; these differ from Milestones in that they are communicated as rewards before the party undertakes the associated quest or goal (as much as possible). This allows the players to have a reasonable understanding of how to advance their characters in level.

When the party achieves the associated goal, they receive the number of Keystones set as a reward for attaining that goal. Usually this will be 1, but more difficult or lengthy goals might have 2 Keystones set as their reward. Once the party receives an amount of keystones equal to their number (a party of 5 would need 5 keystones), they may level up when they take their next Safe Rest.

The party can earn Keystones through three broad methods.

The first method is simple: complete quests. Each quest will have its keystone reward communicated to the party at the outset, as well as clear conditions needed to earn it.

Example 1: when the party reaches port and undertakes a Safe Rest, they hear a number of rumors, including the rumor that Deadhand Phillip, a notorious pirate hunter wanted “dead or alive” by the Pirate Council of Eight, has been spotted near a known landmark a few days sail from port. At this point, the DM communicates to the players that successfully capturing or killing Deadhand Phillip will reward 1 keystone; achieved when they either bring him in irons to the Council, or bring them proof of his death.

Example 2: the party spots an uncharted island and weighs anchor, intending to go ashore and forage for food, water, and materials for repairs. During their exploration of the island, they uncover a ruin of the ancient world—some sort of temple apparently undisturbed since it was abandoned millennia ago. At the moment this temple is discovered, the DM informs the party that successfully exploring the temple—a classic D&D dungeon—will reward 1 keystone.

The second method is also straightforward: amass treasure. The following table (roughly based on the gold-per-level table from Nimble) lists the amount of gold pieces a party of the specified level would need to successfully bring back to safe port in exchange for 1 keystone.

Level gold Level gold Level gold
1 200 7 5,000 13 65,000
2 320 8 8,000 14 100,000
3 640 9 12,000 15 150,000
4 1,200 10 20,000 16 250,000
5 2,200 11 28,000 17 350,000
6 3,000 12 40,000 18 500,000
19 1,000,000

This includes, of course, valuables and trade goods; it need not literally be gold. The value counted toward the keystone will be equal to the amount of gold you actually receive when selling. Wheeling and dealing certainly helps! If the party decides to keep any particular items instead of selling them, the “base” market value will be used. Recovered food, water, and ship repair supplies do not count toward amassed treasure.

This wealth also does not need to stay in the party’s possession—or their safe-port “bank account”—to be counted. Spending gold at safe port counts as bringing it back safely, no matter what is purchased: supplies, upgrades, a night (or ten) of carousing, etc. On the other hand, paying gold as a bribe to patrolling port authorities to avoid arrest before reaching safe port does not count toward a keystone (unless, say, someone in the party sneaks aboard their ship and steals back the bribe, plus interest).

The third method is a catch-all category for other great deeds the party achieves. If during the course of this campaign the party achieves something truly astounding, the DM may choose to reward them a keystone then and there. For instance, on a particularly unlucky random encounter roll, the party might manage to literally slay the Kraken. 5 levels earlier than expected. Somehow! You’d have to see the dice rolls to believe it. That is more than worthy of a keystone, even if it can’t be predicted in advance!

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