yeah, I’ve been in so many companies where “sweetheart deals” force the use of some really shitty tech.

Both when the money has been actually committed and when it’s usage based.

I have found that companies are rarely rational and will not “leave money on the table”

That is how the sausage is made. Ironically this is what democratic institutions like county admins etc are ridiculed for due to more transparency compared to private sector.