Does the description disclose side effects, auth requirements, rate limits, or destructive behavior?

With no annotations, the description carries the full burden. It usefully discloses non-obvious rendering behavior (Markdown subset, checklist conversion, and that checklists are NOT To-dos), which is real value. However it omits permissions, duplicate-title behavior, and never states what the call returns — the id is only implied by 'this note's id', which matters for chaining into create_task.

Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

Is the description appropriately sized, front-loaded, and free of redundancy?

Three tight sentences, front-loaded with the core action, then format semantics, then the To-do routing rule. Every sentence carries information; the only mild bloat is the mixed audience of formatting and cross-tool routing in one paragraph.

Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

For a 4-parameter write tool with no annotations and no output schema, the description covers format and To-do routing but leaves the agent guessing about the return value (needed to link via create_task) and about behavior when the same title already exists. Adequate but with clear gaps.

Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

Schema coverage is 50%: workspace and collection are documented in the schema, but title has no description anywhere. The description compensates well for content by spelling out the Markdown semantics and checklist behavior, but adds nothing for title or the workspace/collection selection logic beyond what the schema already says. Baseline 3 fits.

Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

Does the description clearly state what the tool does and how it differs from similar tools?

The description opens with a specific verb and resource ('Create a note in Caddie') and immediately distinguishes the tool from create_task for the To-do case. It does not distinguish itself from append_to_note, update_note, or note_from_template, which share the note-creation space, so sibling differentiation is only partial.

Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

Does the description explain when to use this tool, when not to, or what alternatives exist?

It gives a clear routing rule: '- [ ]' lines are checklist items in the note, and to give the user a real To-do use create_task with note: <id>. It also says where to put decisions ('in your reply'). It stops short of covering append_to_note vs create_note vs note_from_template, so it is not a full when/when-not map.

Agents often have multiple tools that could apply. Explicit usage guidance like "use X instead of Y when Z" prevents misuse.