Tony's Mac + iOS Productivity Stack: Full Audit & Recommendations

Compiled from conversations on May 4 & 10, 2026. Covers task management, calendar, app ecosystem, Setapp, Dropzone 5, and the Obsidian ↔ Synology backup workflow.

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Executive Summary

This report synthesizes the full stack audit from across several conversation threads. The core finding is that Tony has a sophisticated, well-reasoned productivity system built on GTD-context routing, Johnny Decimal (JD) file organization, and Obsidian-centered PKM — but has accumulated significant app sprawl in four categories: task management, notes, email clients, and storage. The recommended path is consolidation, not migration. Stay on Todoist; swap Apple Calendar for Fantastical; rationalize notes to Obsidian + Notion + Craft; and build Dropzone 5 as the operational "filing muscle memory" layer that connects daily file handling to both the Obsidian vault and the Synology NAS.

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Part 1: Task Manager & Calendar Decision

The Three Options Evaluated

Why Not Google Tasks + Google Calendar

Google Tasks is too lightweight for a GTD-context routing system. It has no projects, no filters, no labels, and no real GTD support. While Google added native time-block dragging from Tasks into Calendar in late 2025, that feature alone does not compensate for the structural limitations of Tasks as a capture and processing environment. Switching would mean dismantling an entire Todoist project architecture for something categorically weaker.

Why Not Things 3 + Fantastical

Things 3 is a genuinely excellent GTD-native task manager with a calm, opinionated UI. However, for this specific stack it has three disqualifying constraints:

• No web version and no IFTTT integration — existing automations would break
• No team or cross-platform collaboration — relevant for a nonprofit director role
• One-time purchase (~$80 total across Mac + iPhone + iPad) with no task-sync back to Obsidian or Notion workflows

The only scenario where Things 3 is the right call is a full commitment to Apple-native, automation-light workflows — not the current direction.

The Recommended Stack: Todoist + Fantastical

Todoist stays. The entire GTD routing system, JD-tagged project structure, IFTTT hooks, and Perplexity Tasks templates are already built on Todoist. Todoist's natural language input, recurring tasks, filters, and labels map directly onto the "every item must have a destination" doctrine. Todoist Assist (AI features, 2025) further aligns with the personal COO workflow.

Fantastical replaces Apple Calendar. The upgrade case is strong:

• Direct Todoist integration — Fantastical pulls Todoist tasks into the calendar timeline, unifying tasks + events in one view
• Natural language input on mobile — critical for fast mobile entry
• Calendar Sets — focused views per context (work vs. personal) without toggling individual calendars
• Superior widgets — interactive, filterable, and far more functional than Apple Calendar's
• Meeting integrations — Zoom, Google Meet auto-parsed from invites

Cost is ~$57/year. Given Fantastical is part of the Setapp subscription Tony already maintains, this upgrade has zero marginal cost.

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Part 2: Full iOS App Audit

App Sprawl: The Four Critical Overlap Zones

Task Management (Reduce to 2)

Notes / PKM (Reduce to 4)

Email (Use 1 Primary)

Storage (Consolidate)

Setapp Stack (Already Justified)

The following confirmed Setapp apps collectively justify the subscription alone:

• Fantastical, Craft, TextExpander, Cardhop, Paste, Drop Share, CleanMyPhone, Orion (browser)

iOS companion apps extend the value to mobile seamlessly.

AI Stack (Intentionally Plural — Keep All)

Each tool has a distinct, non-redundant role:

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Part 3: Mac Desktop App Audit

Confirmed New Mac-Only Tools

System Glue Layer

Launch & Control   → Alfred, BetterTouchTool, Bartender
Linking            → Hookmark (top projects only)
Time Awareness     → Timing, RescueTime
Drag-and-Drop      → Dropzone 5 (Yoink for overflow)
Clipboard/Snippets → Paste, TextExpander
AI Lab             → Ollama, Prompt 3, AI Council

TextExpander: The Underleveraged Power Tool

With 1,200+ snippets, TextExpander is a keyboard-level command palette on both Mac and iOS. Recommended upgrades beyond current group-invoked usage:

• ;jd35 → expands full JD 35.xx taxonomy for tagging
• ;taskroute → expands the GTD routing checklist ("every item must have a destination")
• ;weeklyreview → expands Claude weekly review prompt template
• ;nonprofit → expands boilerplate grant language blocks
• ;jdpath → expands a current project's full JD path for quick note headers

Since TextExpander is keyboard-level on iOS, every input field — Drafts, Spark, Todoist, Obsidian — becomes a snippet command palette.

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Part 4: Dropzone 5 — Obsidian & Synology Build-Out

Overview

Dropzone 5 (released March 2026) is a drag-and-drop grid utility for macOS. Its role in this stack is narrow and specific: serve as the front door for filing files into Obsidian vault folders and sending vault backups to Synology, replacing repeated Finder navigation.

New Dropzone 5 features relevant to this stack:

• Multi-grid support — separate grids for "Obsidian Ingest" and "Synology Backups"
• Per-grid Drop Bars — file staging shelves per context
• dz CLI integration — scriptable from Terminal and Alfred
• Custom folder icon inheritance — picks up macOS Tahoe folder colors/symbols
• Per-action keyboard shortcuts (Pro) — trigger actions without dragging

Assumed Folder Structure

~/Obsidian/TAC2025.1/
├── 00 Inbox/
├── 15.02 Research/
├── 35.03 Grants/
│   └── Attachments/
└── 99 Assets/

~/Synology/Backups/Obsidian/
├── VaultZips/
├── DailyNotes/
├── Config/
└── ManualSnapshots/

The 8 Dropzone Actions

Grid 1: Obsidian Ingest

Grid 2: Synology Backups

Behavior note: Ingest actions use Move (file is filed permanently). Backup actions always use Copy (source stays on Mac; Synology receives a duplicate).

Step-by-Step: Creating Each Action

Prerequisites: Create all 8 destination folders in Finder before starting. Confirm Synology is mounted and its path is accessible.

Step 1 — Create the two grids:

1. Open Dropzone 5 → Settings → Grids
2. Create Obsidian Ingest grid
3. Create Synology Backups grid

Step 2 — Add each folder action (repeat for all 8):

1. Open the relevant grid
2. In Finder, locate the destination folder
3. Drag the folder onto Dropzone's Add to Grid area
4. Rename the action using the names in the table above
5. Set Move/Copy behavior per the table
6. In Preferences, assign the keyboard shortcut (Dropzone 5 Pro)

Step 3 — Test each action:

1. Select a dummy file in Finder
2. Press a shortcut (e.g., ⌃⌥⌘G)
3. Confirm the file lands in the correct destination folder
4. For backup actions, confirm the original file remains in place

Global Shortcut

Set ⌃⌥⌘D in Dropzone Preferences → General as the Show Dropzone grid toggle.

Keyboard Shortcut Mnemonics

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Part 5: Daily File Flow (User Flow)

flowchart TD
    A([📥 File Arrives\nDownloads / Email / Web Clip]) --> B{Do I know\nwhere it goes?}

    B -- Yes, filing it now --> C[Open Dropzone\n⌃⌥⌘D]
    B -- No, triage later --> D[📥 Obsidian – 00 Inbox\n⌃⌥⌘I]

    C --> E{Which JD area?}

    E -- Research material --> F[📄 Research 15.xx\n⌃⌥⌘R]
    E -- Grant/nonprofit doc --> G[📑 Grants 35.03\n⌃⌥⌘G]
    E -- Image/media/PDF embed --> H[🖼 Assets 99\n⌃⌥⌘A]

    D --> I[Triage in Obsidian\nduring weekly review]
    F --> J([File lands in vault folder\nReady to link in Obsidian])
    G --> J
    H --> J

    subgraph Backup Workflow
        K([Trigger: End of week\nor before major vault change]) --> L{What changed?}
        L -- Vault ZIP ready --> M[🗂 Vault ZIPs → Synology\n⌃⌥⌘Z]
        L -- Daily notes exported --> N[📅 Daily Notes → Synology\n⌃⌥⌘Y]
        L -- Plugin/theme changed --> O[⚙ Config → Synology\n⌃⌥⌘K]
        L -- Pre-refactor snapshot --> P[📦 Manual Snapshot\n⌃⌥⌘S]
        M --> Q([Synology NAS\nHyper Backup versions it])
        N --> Q
        O --> Q
        P --> Q
    end

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Part 6: Rationalized Full Stack (Reference)

Recommended Production Stack

Apps to Cut or Demote

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Part 7: Mystery Apps — Unresolved

Two app references from voice dictation could not be confirmed:

• "psychology" — appeared as "Secure SignIn by psychology" and "photos by psychology." Likely a garbled dictation for 1Password or another password/identity app. If confirmed as a second password manager alongside Bitwarden, one should be removed.
• "TCA" and "pertain" — not yet identified. Follow-up needed before auditing these.

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Conclusion

The core stack is sound. The routing doctrine ("every item must have a destination, every destination must be auditable") is the right framework, and the tools largely support it. The remaining friction comes from accumulation — too many apps doing similar things. Three moves close most of the gap:

1. Cut ClickUp and Trello from task management; keep Todoist as the single truth.
2. Swap Apple Calendar for Fantastical — zero cost on Setapp, meaningful daily gain.
3. Build out the 8 Dropzone actions — converts file handling from Finder navigation to muscle-memory hotkeys, directly wiring daily work into the Obsidian vault and Synology backup chain.

TextExpander's 1,200-snippet library is the most underleveraged asset in the stack. Treating it as a routing accelerator — not just a text shortcut tool — is the highest-ROI upgrade available without buying anything new.

15 Notes link here

Note
2026-06-16
2026-07-15
2026-07-22
lint-run-2026-07-21_19-42-57
lint-run-2026-07-21_19-50-17
lint-run-2026-07-21_19-52-56
lint-run-2026-07-21_20-07-05
lint-run-2026-07-21_20-08-12
lint-run-2026-07-21_21-36-52
lint-run-2026-07-21_21-38-38
lint-run-2026-07-21_21-39-16
lint-run-2026-07-21_21-39-30
lint-run-2026-07-22_00-40-30
lint-run-2026-07-22_02-30-54
lint-run-2026-07-25_17-22-00