AI / GenAI·6 min·24 September 2026·Which AI assistant? — Part 6 of 6

Which AI assistant? To pay or not, and for which one

This is the part the series started for: “Should I pay, and for which one?” Over five parts I’ve put the five assistants side by side, and the answer fits in three sentences. Start free. Pay only once you’ve hit the same wall three times. And then pay for one, not two.

This is part 6 of 6. The earlier parts covered free versus paid, search, making it personal, where your question goes and work. This part draws the conclusion.

The decision tree

Question one: are you hitting anything? If not, stay free. That isn’t thrift, it’s what the earlier parts showed: search, memory and a standing instruction are in the free tier at almost all five, and the training setting is the same on paid as on free. Paying doesn’t buy you privacy, only room.

Question two: what’s the wall? There are three, and each points a different way. If you’re hitting the limit, a chat that stops halfway or a wait on a productive afternoon, you buy usage. That’s the entry tier around twenty euros at each of the five. If you’re hitting memory, explaining who you are every time, you often don’t need to buy anything: write the standing instruction from part 3. If you’re hitting a connection, wanting your mail or your files in there, that’s the real paywall, and then you look at which tool has that connection.

Question three: which one, then? Not the best one, but the tool that’s already in your day. If you live in Gmail and Drive, Gemini is the obvious candidate, and the five-euro tier does more there than you’d expect. If you mostly look things up, Perplexity. If you work on one thing for a long time, writing, building, figuring out, then Claude or ChatGPT, and the difference between those sits less in the model than in what comes around it; part 3 has the table. Grok is the answer if you want news from X, and otherwise not.

Question four: two free or one paid? For someone who types something in now and then, two free versions beat one subscription. You get the strong side of each, you’re locked in nowhere, and you learn where your wall is before you pay for it. Someone who works with it every day is better off with one paid account that holds everything, because the setup from part 3 otherwise ends up scattered across two tools.

The table

Checked on 6 September 2026. The prices come from part 1, the rest from the parts after it.

If your wall isThen you pay forPer monthOr you do this for free
Limit or waitUsage: Plus, Pro or Google AI ProAround 20 eurosTwo free accounts side by side
Explaining yourself every timeUsually nothing0A standing instruction of three sentences
Mail or files in thereConnections: Perplexity Pro, ChatGPT depending on your plan, Gemini through the Workspace app with activity on5 to 23 eurosOne custom connection free at Claude
News from XOnly Grok has it0 to 8 dollarsA free X account
More than a hundred eurosMax, Pro or Ultra90 to 230 eurosNot for this reader

What I see myself

My own choice runs against the decision tree, and that’s worth explaining. I pay for Claude on the heaviest plan, and that didn’t start with a wall but with wanting to support the team; part 1 tells that story. I’ve never cancelled a paid AI subscription.

If I could keep only one paid and one free: Claude paid, Gemini free. I didn’t give a reason for that, and I’m not filling one in here; it’s the combination that’s left. ChatGPT and Perplexity stay free, and behind that sits an exception that only applies to me: the separate credit for Perplexity’s developer interface from part 1.

Caveat: the bill the table doesn’t show

The earlier parts showed three costs that aren’t in euros. At three of the five the training switch defaults to on, and ChatGPT and Perplexity say outright that paying changes nothing there. Everything you set up to make an assistant personal stays behind when you switch. And a free account on your work email address can end up with your employer’s administrator. None of those three change when you pay. The decision tree above is about money; those three are about what you put in.

The second caveat is that this series is a snapshot. Each part carries the date its prices and rules were checked, and a change shows in that date. But the direction of the decision tree, free first, pay at a wall, one instead of two, isn’t tied to a price.

What to do tomorrow

Write on a note which wall you hit in the past month. If there’s nothing on it, stay free and you’re done. If there is, the table points at what you buy, and you buy it for one month before you buy it for a year.

Frequently asked questions

Which AI assistant is the best?

After six parts I can’t answer that question, because the five don’t differ on one axis but on search, memory, connections and privacy. The best one is the tool already in your day whose wall you know.

Is twenty euros a month worth it?

If you’ve hit a limit or a wait three times, yes, and otherwise no. Pay for one month first. If you notice nothing after that month, you didn’t need it.


Sources: the prices and rules in this part come from the source bundles of parts 1 to 5, checked on 6 September 2026: Claude pricing, ChatGPT pricing, Gemini subscriptions, Perplexity Pro, X Premium, Gemini Apps Privacy Hub, Claude consumer terms.