A lot of the driver here is not in the moment short-sightedness, but rather a byproduct of the procurement or other finance processes (ironically often instituted with intent to prevent waste and fraud or make the company more efficient).

It’s not just the $250/yr/dev, but rather the requirements to create a new vendor in the ERP morass, to get approvals for an exception to the standards for payment terms (and/or methods), any requirements for vetting vendors, etc.

If you’re selling to an enterprise, don’t charge just above whatever the “employees can put it on their card without approval”. If you’re going to exceed that, you might as well exceed it by a lot. (If you’re going to make every developer file an expense report every month, I can readily prefer to do a lot of command line typing rather than filing an expense report… If I automate that for a lot of my fellow devs, I get to do something fun and be a minor folk hero.)

https://www.joelonsoftware.com/2004/12/15/camels-and-rubber-...