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There is also a potential hardware upgrade element to consider too. Some XP kit is too old to run Win 8.1 esp if going for 64 bit version which, as you say, then needs a whole software compatibility testing effort before making the upgrade. Can be expensive, but the leap cannot be put off...

I did a desktop migration project for a well known [house-hold name] org last year. We went from XP to 8.1 and several times we discussed changing that to Win 10 but stuck with 8.1 Main logic was concern for availability of Win 10 drivers for older legacy peripheral kit - printers, scanners and...