Some decision are hardware driver driven:

I still have one machine on my network running 98SE with parallel port outputs to a still working tabloid size laser printer and a XY pen plotter modified to use Sharpies. It is stable and during weekly maintenance and B/U it is rebooted.
The plotter is great for superimposing change orders onto drawings with different colours. To replace the tabloid printer with the multiple input and output options is over $4k+

I will keep at least one XP box for it is running drivers for my Nikon 9000 Scanner.

No need to buy new fruits every time there is a new crop.