If you have many pages the maintainability will be completely shot. I recommend designing your layout in such a way that you can reuse styles across pages. I bet that even with whatever cool stuff you have in your pages, you can find a way to share/inherit styles such that the size of your stylesheet does not go out of control.
And as an aside, I would tell you not to worry about the size of your stylesheet. Build it the way you need it built. It will only be downloaded once, and then cached, so you will be fine. If you have a separate stylesheet for each page, however, thats when your user needs to download more than they have to, which could slow things down even more than having just one big sheet.