The Five Windows Productivity Apps Now Carry a $552 Bill

Five popular Windows productivity apps now run about $552 a year if you buy the paid tiers those roundups treat as the real product. Todoist, Trello, Obsidian, RescueTime, and Notion still do useful work on a PC.

Reminders, extra board views, long history, and full AI now require paid plans, and Windows 11 already ships overlapping tools for lists, notes, and focus.

The Five-App Stack Now Costs $552 a Year

The usual pitch is that these five apps turn a plain Windows install into a proper work setup. Each one still covers a distinct job: fast task capture, visual boards, local notes, automatic time tracking, and a flexible workspace. The second bill is the paid plan that makes that job feel complete.

Add the annual rates those vendors list for one person and the stack is $552: Todoist Pro at $60, Trello Premium at $120, Obsidian Sync at $48, RescueTime Solo at $84, and Notion Business at $240. You can spend less by staying on free tiers. You then give up the features the same roundups use to call the apps capable.

THE FIVE-APP YEARLY BILL

Microsoft does not charge extra for To Do, the Clock app, Sticky Notes, or Copilot on Windows. Copilot in OneNote is the exception, because it needs a Microsoft 365 Personal, Family, or Premium plan for the account owner. That is still one vendor bill, not five.

Todoist Raised Pro After a Quiet December Change

Todoist remains the low-friction list: type a sentence, get a task, including a recurring one, without hunting through menus. The free plan still caps you at five active projects, which is enough for a short trial and tight for a life split across work, home, and side projects. Pro lifts that cap to 300 projects and adds the calendar layout, reminders, and the extra filters people actually miss after a week.

Doist raised Pro pricing on December 10, 2025. Monthly billing moved from $5 to $7, a 40% jump. Yearly billing moved from $4 a month ($48 a year) to $5 a month, which is $60 a year, a 25% jump. App Store subscribers can stay on a Pro Legacy rate; everyone else rolls onto the new price at the next renewal.

This price update helps us keep investing in Todoist sustainably while delivering a reliable and secure experience.

Todoist, Pro pricing update

Microsoft To Do already handles multiple lists, due dates, recurring tasks, and a My Day view, and it ties into Outlook and Microsoft 365. Todoist still wins if you live on natural-language capture and shared household lists. It is no longer the $4-a-month habit it was before that December invoice.

Trello’s Free Board Hits a Ceiling Fast

Trello is still the gentlest board on a Windows desktop or in a browser: a card is a task until it grows checklists, files, and due dates. The free workspace is not a toy, but it is a box. You get 10 boards, 250 automation runs a month, and 10 MB per file.

Paid seats are where the product the roundups describe actually starts. Trello’s pricing page lists Standard at $5 and Premium at $10 per user per month on annual billing, or $6 and $12.50 billed monthly. Standard unlocks unlimited boards, custom fields, card mirroring, and 1,000 automation runs. Premium adds AI on the boards, plus Calendar, Timeline, Table, Dashboard, and Map views. Enterprise is $17.50 per user per month, $210 a year.

Windows has no inbox Kanban app that matches that drag-and-drop board. Calendar and To Do can hold dates and lists. They will not replace a renovation board or a job-search pipeline. If the visual board is the job, Trello is the one app in this set with no Microsoft twin. Power-Ups, extra views, and plugin rabbit holes still add a quiet setup tax after you install them.

Obsidian Still Gives Away the Notes App

Obsidian is the outlier because the core app is not a teaser. Notes are plain Markdown files on your drive, no account, no feature gate on the editor for personal use. Uninstall the app and the files remain readable. That is the ownership pitch, and it still holds.

The paid extras are optional services. Sync is $4 per user per month billed annually, $48 a year, with end-to-end encryption, version history, and shared vaults. Publish is $8 per site per month billed annually. Catalyst is a $25 one-time badge for early betas. Commercial licensing is $50 per user per year. Students, faculty, and nonprofit staff get 40% off Sync and Publish.

People who treat notes as a long-term archive now keep them as local files for that reason, then let other tools read the same folder. Andrej Karpathy described that pattern in April 2026, using Obsidian as the window onto a markdown wiki an LLM maintains.

I use Obsidian as the IDE “frontend” where I can view the raw data, the compiled wiki, and the derived visualizations.

Andrej Karpathy, on X

OneNote covers notebooks, sections, handwriting, and file attachments, and Copilot in OneNote can draft lists if you already pay for Microsoft 365. It does not give you a folder of files you can zip, grep, and copy when a vendor changes terms. That is the job Obsidian still does without a monthly seat.

Lite RescueTime Keeps Only Two Weeks

RescueTime’s pitch is that you should not have to remember to start a timer. It logs apps and sites in the background, then shows where the hours went. That honest picture is the product. The free Lite plan still tracks. It does not keep the picture.

RESCUETIME LITE VERSUS SOLO

• Free history: Lite keeps two weeks of reports, not a season of habits.
• Solo Focus: Solo Focus at $7 a month billed annually, $84 a year, or $9 month to month.
• Solo+: $12 a month billed annually ($144 a year), or $15 month to month, if you need timesheets.

Paid Solo Focus adds Focus Sessions with blocking, alerts, offline tracking, detailed window titles, iOS tracking, and unlimited report history. Team Focus is $10 per user per month on annual billing. The company told long-time users that grandfathered rates held through April 15, 2026, and that changing or cancelling a plan moved an account onto the new sheet.

Windows Clock already runs focus sessions, counts daily focus time, and can pull tasks from Microsoft To Do. That is a nudge, not a background log of every app. Recall on a Copilot+ PC is closer to a timeline of what you saw, and it is a different product: opt-in snapshots, encrypted on the device, opened with Windows key + J, and limited to machines with a 40 TOPS NPU, 16 GB of RAM, and 256 GB of storage, plus 50 GB free. Most Windows PCs do not get it.

Notion Folded Full AI Into Business

Notion is still the blank page that can become a meal plan, a budget, or a light project tracker. That flexibility is the trap as much as the draw, because a Saturday can vanish into databases. The 2026 change is that the AI teammate the company now sells is no longer a bolt-on for cheap seats.

Notion’s help center says Notion AI is only available on Business and Enterprise. Free and Plus users get a limited trial. Current plan tables matching the public pricing page list Plus at $10 per member per month and Business at $20, billed annually, with monthly rates about 20% higher. Business is $240 a year for one person. Custom Agents then meter extra work at $10 per 1,000 monthly Notion credits. Workers, still in beta, start using credits on October 15, 2026.

THE PRICE MOVES

1. December 10, 2025: Todoist Pro moves to $7 a month, or $60 a year.
2. May 4, 2026: Notion Custom Agents begin spending Notion credits.
3. October 15, 2026: Notion Workers leave the free-to-try window and start using credits.

The old $10-a-month AI add-on is gone for new buyers, so the cheapest path to meeting notes, the Notion Agent, and enterprise search is a Business seat. People who liked Notion as a notebook keep leaving after that paywall, not because a page failed, but because the product now wants to be an AI workspace. Plus is still free for eligible students and educators on a one-member workspace. That discount does not restore full AI.

Microsoft Already Put a Task App on the PC

Microsoft’s own guide, dated February 19, 2026 and updated March 25, 2026, ranks built-in Windows productivity apps already on the PC in a list that starts with Copilot and Microsoft To Do. The company is not hiding the overlap. It is publishing it.

THE INBOX JOBS THESE FIVE APPS DUPLICATE

• Tasks: Microsoft To Do already does lists, due dates, recurring work, and My Day, with Outlook and Microsoft 365 hooks.
• Notes: OneNote holds notebooks, handwriting, audio, and files; Sticky Notes covers the short reminders.
• Focus: Clock runs timed sessions and daily totals, and it can pick a To Do task for the block.
• Capture: Snipping Tool still uses Windows logo key + Shift + S, and Edge Collections file research without a new account.
• Boards: Nothing in that inbox list is a Trello-style Kanban board, which is the hole the third-party stack still fills.

Copilot on Windows can turn scattered OneNote or Word notes into a checklist, summarize a long email, and take a spoken plan. That is Notion-like assistance without a Business seat, with the usual Microsoft 365 limits on the deeper Copilot features. Recall remains a Copilot+ preview with Windows Hello, local encryption, and an off-by-default snapshot toggle. It is not RescueTime, and it is not on a typical office tower PC.

Who Should Still Pay for the Third-Party Stack

The five apps are not duds. They are products whose useful layer moved onto a price sheet while Microsoft filled the same roles for free, or as part of a 365 plan you may already have. Install one on purpose. Installing all five at paid rates buys a second office suite.

WHO THE PAID SEATS STILL FIT

• Board-first work: Trello Standard or Premium is still the clean buy when the job is cards on a board, because Windows does not ship that view.
• Files you must own: Obsidian stays the right notes app when the vault has to survive a shutdown, a terms change, or an export panic, and Sync is optional.
• Shared lists across phones: Todoist Pro is still easier than To Do if the household already lives in that inbox, and $60 a year is the cost of keeping it.

RescueTime Solo is a narrower buy: you want a background log, not a focus timer. Notion Business is the narrowest, because $240 a year is the ticket to the AI workspace, not to a notebook. Free Notion still stores pages. It does not include the teammate the company now puts on the homepage.

Trello still earns a slot when a visual board is the actual job. Obsidian still earns a slot when the files have to live on the disk. The rest of the roundup is a paid-plan decision sitting next to tools Microsoft already left on the Start menu.