As a long time windows user and Mac OS hater, I've made the switch 5 days ago and I must admit I was in the wrong. Windows can be a great system, but so is Mac OS. OS X is very intuitive and I found myself discovering features by accident, simply by trying something because it felt, well, intuitive.
A good example is PDFs (I primarily use my laptop for research, so a lot of my work involves going through academic papers) viewed in preview. Just today I was scrolling through a paper that had some graphs in it. Such documents are generally vertically oriented, but then you have to rotate certain pages to view the graphs horizontally. In preview, it was a simple trackpad gesture, while when viewing PDFs in Acrobat Reader on Windows it takes some more effort and it can get annoying... might seem minor but it just represents the point I'm trying to make.
So, I would say that you should be fine and make the switch quite quick. If you are a relatively informed Windows user (as in you quite understand how the file system works and why things happen the way they happen), you won't be struggling.
As far as "pages" and "numbers" go... well I think I'm sticking with MS Office for now. Keynote is supposedly very good, but I have a major presentation on trade policy next week and I think I'll have to use my old windows laptop for that (I haven't got the Office for Mac yet). This might be a matter of time though, I just need the productivity now.
All in all, make the switch, try it out. It's worth it. First three days I had mixed feelings, but I made a strong case of not trying to make my OS X experience as similar to Windows as possible. I can say that after 5 days I am comfortable with the system enough. I imagine it will take another two weeks for me not to miss Windows at all, but I can see it happen.
