I don't know if I have answer to your question but I have switch from a MacBook to a Surface Pro 4 and I guess the learning curve isn't that steep considering the amount of information in this forum (Especially when you need help with the bugs SP4 comes with). Windows 10 is pretty easy to navigate and customise.
If you're thinking of switching platform you must be prepare that there might be some small little bugs that might annoy you. For instance, the sleep to wake time is considerably slow compared to a MacBook, it loses more battery juice while sleeping compared to MacBook, etc. All these small little things doesn't really put me off though, I overlooked all these flaws for the fact that this is a productivity workhorse for me. The ability to write, draw and touch is really a big plus for me. It makes this device so versatile in any circumstances. I can get everything done on windows! :grin:
As for the bugs and glitches reported, Microsoft is solving it diligently. You can always see updates coming so I am still pretty confident all issues will eventually be addressed! Rocking a i5/8/256!
Easy. If all you're going to do, productivity wise, is type a document and play angry birds or whatever generic game, then the iPad pro is perfect. Be aware, it's more expensive... Surface pro 4 comes with 128 gb and the iPad pro 32 for base models. Expandable storage is a no go on the iPad, but you can get SD cards much cheaper for the surface pro, 128gb extra was 30 euros on amazon.
Ports like usb thumb drives, printers, scanners all work with Windows since it's a full PC. You can't use anything on an iPad that isn't a Bluetooth keyboard sadly.
If you want a computer, surface pro 4. If you want a tablet then any Android or iPad will work. I like to truly multitask, so the surface was the only brand name option for me.