My experience has been that companies tend not to buy software updates when first released due to concerns about early bugs being found and problems occurring.In fact,unless they have one of the expensive maintenance agreements in place they only tend to buy when a clear advantage becomes apparent.The other trigger to updating can be the arrival of files from customers with newer versions of software that can only be read by the updated version and I have known one company that would buy a copy of the new software and then use it to save in the file format that the other computers in the office could read.
The example of Mastercam is a good one;I found V8 good and V9 absolutely great and that was when using a computer that was pretty high spec at the time.Now my two year old phone has much more processing power and any computer would hardly notice the workload of running a program from that era.An awful lot of users are simply cutting basic outlines and holes and as such have no need for super whizz bang capabilities.I can recall that Mastercam 9 with all the trimmings could thread mill,surface in several different ways and much more besides.If you had paid the maintenance from then until now,what extra capabilities would you have gained and at what cost?
At the start of this thread we saw how the OP was using an online service to generate a toolpath and might have got one if he made all the correct choices.We have seen that software developers like to introduce new things in order to stay in a job and I totally agree with the point that Freecad needs a benefactor to coordinate and document progress.Even without one I will continue to use it as the combination of capabilities and price coupled with a post processor that works for me are just outstanding.