I agree that is part of the problem, but I think the real problem is that even if you accept the premise that it would take just a weekend it is still the wrong analysis for the company. Even a job that you can complete in an hour is easily $100-200 worth of direct engineering costs.

I think the real problem is that most developers naturally plug in the value of their time on a hobby project/in school (which is ~$0/hr) when deciding if a time-cost tradeoff is worthwhile. Since the answer is almost always no if you incorrectly value time at $0/hr and management usually can not do the analysis themselves, management pattern matches and determines that spending money on developer tooling is essentially never worthwhile and that sums like $5k (which few people would spend on personal projects) are outrageous. If the correct time-value analysis was done, you would get outcomes more like electrical engineers (who generally make less than high-end software developers) where companies will spend literally $50k/yr/engineer on tooling to make them 50% more productive since that actually makes perfect business sense based on the amount they are being paid. In contrast, if you went to management in a software company pushing for a $50k/yr/developer expense they would probably laugh you out of the room or require some totally outrageous improvement like 10x for everybody.

Indeed, this is visible at personal and corporate level. I've seen companies balk at a Total Commander license which is negligible.

I've also had corporate procurement waste my time on a project for a potential $200 sale which never materialized.