Oh for sure from DOS to 95 it was a whole new world and maybe I'm looking at it as being a non average user but I don't see there being a steep learning curve between 95 and 8.1. It was pretty gradual over time with 8.1 being more like a tablet. If you are a tablet user you should be able to pick up on 8.1 pretty quick. As far as office I haven't used the MS version to any extent in many years
They had pretty much the same release date but general updates are done far more often on android devices than Apple devices. Maybe it's out of necessity I don't know but I do know I've done updates on my wife's tablet at least 3 times since Christmas I don't believe I've updated the I devices at all
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IMO, it was easier for users to go from Dos / Win3.11 to 95 than it was to go from XP or 7 to 8 / 8.1 .. and I'm referring to the average user. From a tech standpoint, it was not easy as well because just like in Office, they moved everything around. What took a tech 3 mins to do in Win XP / 7 took easily double that in 8 / 8.1. Also not good for production environments. For the average user, it took even longer.
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