What money is that?
What for?
Windows has indeed put out a couple of OS’s that were not exactly the cats meow, (like ME) but I have only purchased one paid for update and that was windows 7, when it first came out and Ive been running it ever since for several years now..
In fact the computers I have running it are just about too old to update to 10 but since it’s free...I am taking it.
So 95% of the time, I upgrade OS’s at the same time I buy new gear. I have spent no money other than that one upgrade for 90 bucks. I too started with 3.2 and DOS, and then went to 95.....etc