Historically, Apple absolutely would have been the risky platform to go for (I waited until their Intel laptops, using Boot Camp as an insurance policy). But these days people have iPhones, iPads, some even have Apple TVs... the Apple hardware ecosystem is actually far stronger than Microsoft's. You absolutely are risking that syncing with your iPhone etc will be worse.
iPhone market share in the US is 43%. Macbook market share is 12%. So the vast majority of iPhone users are "risking" this.
Which is really not a risk at all, because if it really were a risk Apple would be shooting themselves in the foot. They would be killing one of their most successful products for the sake of some of their least.
The Microsoft hardware product line is arguably more complete than Apple's at this point, when you factor in the Xbox. There's minimal risk to casual users in switching.
I find it very interesting that Apple is now the "default" laptop and Windows is the strange alternative that people are worried about switching to.
Only in a tiny minority of wealthy dev/artist types.
It'd help a lot if Microsoft manages to get .NET applications to become popular on OSX. That's only possible since this year, and it'll probably take a few more years for applications to become properly crossplatform.
The Surface line is not as flexible. It's perfect for people who are immersed in the Windows world, but a lot of people are not anymore.
The press tends to treat Microsoft like Cinderella's stepmother treated her: unreasonably critical.