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State of Obsidian TTRPG plugins - Jeremy Valentine thumbnail

State of Obsidian TTRPG plugins - Jeremy Valentine

Nicole van der Hoeven·
5 min read

Based on Nicole van der Hoeven's video on YouTube. If you like this content, support the original creators by watching, liking and subscribing to their content.

TL;DR

Calendarium is a ground-up rewrite of Fantasy Calendar designed to be faster and more reliable, especially under sync services that previously caused data loss.

Briefing

Obsidian’s TTRPG ecosystem is shifting from “D&D-only convenience” toward reusable, system-agnostic tooling—largely driven by Jeremy Valentine’s plugin rewrites and new engines. The biggest change highlighted is Calendarium, a ground-up replacement for Fantasy Calendar that’s built to be faster, more reliable with sync, and easier to extend to complex event logic like holidays and repeating patterns.

Valentine describes how his early plugins started as personal, D&D-specific needs, then expanded as other tabletop communities flooded him with feature requests. That pressure pushed him to generalize. Calendarium is the clearest example: Fantasy Calendar accumulated tech debt, and after the original plugin was taken over by the website team (following a naming-collision collaboration), Valentine couldn’t justify fixing the old codebase. He split off a rewritten engine under his own GitHub organization, with centralized automation for releases and updates.

Calendarium is still in beta, but the core is already usable and many users have migrated. The migration process copies calendars from Fantasy Calendar rather than breaking existing data. It detects Fantasy Calendar installations and prompts whether to take control of those calendars. Users can also import event structures that rely on “inline events” (timeline-style span tags) so multiple events can live inside a single note. Valentine emphasizes reliability improvements: sync-related data loss that plagued Fantasy Calendar is addressed, and the plugin is designed to be faster and less buggy.

The feature gap is event spanning across multiple days. Calendarium’s event system is being rewritten to support conditional and rule-based definitions—think “every other Thursday” or “Thanksgiving” logic—rather than hardcoding specific dates. Valentine frames this as the path toward richer calendar concepts like seasons and weather, which are among the most requested upgrades.

The conversation then pivots to Initiative Tracker, which has also evolved substantially. It now includes a player view suitable for sharing with a table, automatic turn and damage logging, encounter and party builders, and options to drive players directly from stat blocks. Valentine walks through how stat blocks can feed initiative data, and how automation can import creatures via notes, inline stat blocks, or external tooling (including a CLI for 5e and Pathfinder 2E). The plugin is increasingly system-aware: it supports custom XP systems (including Lazy GM-style thresholds), condition amounts for Pathfinder-style decrementing effects, and a growing layout system that lets users customize how information appears.

Finally, Valentine touches on broader plugin strategy: he’s aiming for harmony across systems without forcing every feature to be rebuilt from scratch. He notes that plugins should still function without optional dependencies—users lose benefits but not core functionality. Looking ahead, he flags two major priorities: revamping Fantasy Stat Blocks’ beastiary handling to allow same-named creatures across systems, and completing Initiative Tracker’s layout system so non-HP/AC games can plug in cleanly. The overall message is clear: Obsidian TTRPG plugins are becoming modular engines for time, combat, and data—built to survive sync, scale across rulesets, and reduce manual upkeep for GMs and players alike.

Cornell Notes

Jeremy Valentine’s Obsidian TTRPG plugins are moving toward system-agnostic engines, with Calendarium and Initiative Tracker as the clearest examples. Calendarium is a rewrite of Fantasy Calendar that migrates existing calendars by copying data, improves sync reliability, and supports importing inline events from timeline-style span tags. The remaining major limitation is multi-day event spanning, because the events engine is being rebuilt to support rule/condition-based definitions like holidays and repeating patterns. Initiative Tracker has gained a player view, encounter/party builders, and tighter integration with stat blocks, plus extensibility for XP systems and Pathfinder-style conditions with amounts that decrement each round. Together, these changes aim to make time and combat management less fragile and easier to adapt across different RPG systems.

Why did Calendarium replace Fantasy Calendar instead of patching the original?

Fantasy Calendar accumulated tech debt quickly, and after the plugin was taken over by the website team (triggered by a naming confusion and collaboration), Valentine no longer owned the codebase. With the old structure becoming a source of frustration—especially once it was outside his control—he rewrote the calendar calculation engine from scratch and split the new code into a separate GitHub organization. That rewrite became Calendarium, while the original Fantasy Calendar plugin remains available as the official website-linked plugin.

How does Calendarium migration work, and what does it change (or not change)?

Calendarium is designed to be separate from Fantasy Calendar’s stored data. On first open, it detects Fantasy Calendar and existing calendars inside it, then prompts whether to take control of those calendars. Migration advances the schema and copies calendar data so users can keep playing without losing their existing setup. It doesn’t automatically affect Fantasy Calendar’s own data; Calendarium controls its own imported copy.

What reliability and performance improvements does Calendarium target?

Valentine highlights two practical pain points: sync-related data loss and general fragility. Fantasy Calendar could lose data when used with sync services, and Valentine says Calendarium is hardened against that. He also frames Calendarium as faster and less buggy overall, with a UI improvement compared to the older plugin.

What’s the biggest missing feature in Calendarium right now, and why?

Multi-day events spanning across days are the main gap. The reason is architectural: Calendarium is rebuilding how events are defined. Instead of only supporting start/end date ranges, the new engine is moving toward condition-based definitions (e.g., “every other Thursday” or holiday-style rules). That rewrite is what enables richer recurring logic, but it delays multi-day spanning until the new events engine is complete.

How does Initiative Tracker integrate with stat blocks and encounters?

Initiative Tracker can be driven by stat blocks: creatures marked in stat blocks can become players available for initiative without manually creating them in the initiative UI. It also supports encounter and party builders, saving/loading encounters, and a player view that reflects changes live for the table. Creatures/stat blocks can be imported in multiple ways depending on the system, including inline stat blocks in notes and automated imports via a CLI for 5e and Pathfinder 2E.

What extensibility features make Initiative Tracker less tied to D&D 5e?

The plugin adds an XP system layer so other systems can plug in experience calculations. It also supports Pathfinder-style conditions with amounts and decrementing behavior each round (addressing Pathfinder’s “frightened 2 → frightened 1” style). Valentine also describes a layout system concept for customizing how resources and non-HP/AC mechanics appear, aiming to support systems beyond those built around hit points and armor class.

Review Questions

  1. What technical or ownership constraints pushed Valentine to rewrite Fantasy Calendar into Calendarium, and how does that affect user migration?
  2. How does Calendarium’s planned rule/condition-based event engine change what kinds of calendar events it can represent compared with hardcoded date events?
  3. What mechanisms in Initiative Tracker reduce manual setup at the table (e.g., player view, stat-block-driven players, encounter builders), and how do they support multiple RPG systems?

Key Points

  1. 1

    Calendarium is a ground-up rewrite of Fantasy Calendar designed to be faster and more reliable, especially under sync services that previously caused data loss.

  2. 2

    Calendarium migration copies and controls calendar data separately from Fantasy Calendar, with an initial detection prompt for existing Fantasy Calendar calendars.

  3. 3

    Inline events using timeline-style span tags can be detected and imported into Calendarium, enabling multiple events within a single note.

  4. 4

    The main Calendarium feature gap is multi-day event spanning, delayed by a new events engine that is shifting toward rule/condition-based definitions for holidays and repeating patterns.

  5. 5

    Initiative Tracker now supports a shareable player view, automatic turn/damage logging, and encounter/party builders to streamline combat management.

  6. 6

    Initiative Tracker increasingly integrates with stat blocks so creatures can be driven into initiative without duplicating setup, and it supports extensible XP systems and Pathfinder-style decrementing conditions.

  7. 7

    Valentine’s plugin strategy emphasizes graceful operation without optional dependencies: missing integrations reduce features but shouldn’t break core functionality.

Highlights

Calendarium migrates by copying Fantasy Calendar data into a separate control layer, aiming to avoid breaking existing setups while improving sync reliability.
The rewrite of Calendarium’s events engine is the key to future features like holiday logic and repeating patterns—at the cost of delaying multi-day spanning.
Initiative Tracker’s player view and stat-block-driven players reduce table friction by keeping initiative state synchronized with the underlying notes.
Initiative Tracker’s layout and XP/condition systems are moving it toward broader system support beyond D&D’s HP/AC assumptions.

Topics

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