I happily switch between the two without issue. I've a Win10 laptop at work, an Win10 PC at home, an iMac for Jo, and we use iPhones & iPads when on the go. Really, there's very little in it any more, and both have their good bits and bad bits. The bad bits on both are so few though, I'd go with whatever is cheaper and 'feels' better.
Surface Pro isn't a cheap bit of kit any more either though, however as you say it has the benefit of using a proper OS so I see no reason not to go that way.