I think Mathematica is quite fantastic (took me some time to understand it's patterns). I don't use it currently because 1) A lot of my current work is numerical and not symbolic -- for which Mathematica isn't great; so I use Python/Julia 2) From a long term perspective, I wouldn't want to invest a large fraction of my personal computing efforts into a proprietary single point of failure.
TBH, with regards to paying for software, my psychological motivation is still a work in progress (so the comments above are directed at myself as much as at others), but I'm trying to build a habit of doing it more -- especially to support free software. I care about computing too much -- I would hate to look back on this twenty years later and rue the loss of computing freedom because we were too stingy to invest a hundred bucks a year in the appropriate places.
My point was to combine a compliment (it's a truly awesome set of tools) with a gripe (the pricing is so prohibitive, even decision makers in pretty cost-oblivious organisations cringe when hearing the fees).
I dare say any financial organisation could replace the multilanguaged hell that is user built software by Mathematica and leap forward. It's the licensing cost that make Mathematica a niche product. Microsoft could buy Mathematica and integrate it with Excel (again, partly in jest).