I am often forced to spend a ton of time dealing with tools that don’t work. At my company a lot of meetings start with 10 minutes trying to make the phone conference work. So it’s good use of time to look for tools that work.
Same with Jira. IT bought it and promised to customize it but the last three years they haven’t done anything. so we are now setting it up ourselves. it’s not what we want to do but still the most efficient way to allow us to work.
I don’t know how buying decisions get made but I am pretty sure that user satisfaction is on the lower end of factors that get considered.