People are happy to pay $50/year per seat to have the extra features and to not have to deal with stuff.
There's an issue at the margins here:
$1000/employee is a massive cost - it has to be deeply justified. $50/employee is like ... $2 out of your pocket. It's an incremental cost. The CFO is happy to pay it if there is a lot of value.
A lot of software is in that later category.
Imagine if gasoline was 1 cent per litre - and there was 'free gas' but it was a pain to use, and you had to check a bunch of things. You may just pay the 1 cent.
AI is not quite that yet, but these dynamics will play out eventually, for a lot of things.