Tons of extremely expensive licensed software, with expensive support contracts, and we still spent a ton of time and wrote a ton of Perl to punch them into a shape that worked on our very vanilla installs of Windows 7 enterprise. Contacting anyone's support was invariably an absolute fucking joke of an endeavor. We literally only ever did it when we were sick and tired of bashing our heads against their shitty software and wanted to shelf the project for a week or two to recover our sanity while their support "looked into it" and "escalated our ticket" or whatever.
My experience with whether software was more like Stripe or more like a piano sitting on the sidewalk is that it completely depends on the company's attitude. Either they care that people be able to actually use their software, or they don't. I've seen both huge corporate products and small free software projects that both clearly do not care much about whether someone can get their program working easily.
And I've also seen both paid software and free software that care immensely about getting you started and keeping you going.