Most software companies have no reason to publish this article. A nonprofit that charges per app does, because an app a merchant does not use is a monthly cost that buys them nothing.
Do not upgrade because the business feels busy
Busy is not the trigger. The triggers are structural: you hired someone and a single user is no longer enough, you want the app built for your trade rather than a general one, or manual order handling has started producing errors. If none of those apply, being busy is a reason to celebrate, not to spend.
Do not upgrade to fix a habit problem
If sales are not being recorded consistently today, a more capable app will not change that — it will simply give you a more expensive place to not record them. Fix the routine first. A business recording every sale on the free tier is in far better shape than one paying for an app it opens twice a week.
Do not upgrade for a feature you will use once
An app bought for a single seasonal need costs the same in the eleven quiet months. If the need is genuinely occasional, do it manually and keep the money.
Do not upgrade during your worst month
A bad month makes new software feel like a solution. Usually the problem is demand, price or cost, and none of those are fixed by a subscription. Understand what went wrong first; if better records are genuinely part of the answer, that will still be true next month.
Do not add an app you have not tried
The free tier includes a demo or limited version of a trade app precisely so a merchant can see whether it fits before paying. Use it. An app that does not match how your trade actually works is not worth any price.
What a good reason looks like
A specific thing the business cannot currently do, that costs it money or time now, and that a named app solves. Each app carries its own monthly price and can be dropped again — so the decision is reversible, but it should still be a decision rather than an upgrade reflex.
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