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Apart from it being probably a great app...

"Pay once $149 keep it forever, ongoing compatibility updates + bug fixes, 18 months of new features"

...this is not old skool pay once payment. It is just one payment for 18 months of subscription to new features which makes it slightly more expensive than monthly subscription. Go figure.

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The difference is that with the one-time payment you get to keep the version you have forever, including bug fixes, compatibility updates, and cloud sync, which are all ongoing costs for us.

With the subscription, you lose access when you stop paying.

So I think it is pretty comparable to an old school one-time payment, but with bug fixes and compatibility updates added on top.

The "old skool" was pay once, get (usually) 0 updates and then pay again for a new major version. The keep it but stop getting updates model is better than that, usually.

You mean like Things, which I bought in 2017 and am still getting updates for?

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