Does IE 8 have a limit on number of stylesheets per page?
Solution 1:
Yes, IE8 (and even IE9 apparently) limit the number of style sheets to 31 per page.
Telerik has an article and test page which demonstrate the issue. According to comments in the same article, the 4096 rules per file limitation has been marked as Won't Fix in Microsoft Connect but I've been unable to verify that.
Solution 2:
This thread suggests there is a limit of 31 CSS references per page/CSS file but that you can achieve more than that by using @import and a nested hierarchy of CSS files.
More info from a Telerik blog on the issue making it clearer that this applies to IE8.
Solution 3:
Microsoft claims the limit is 30, but the limit is apparently 31 according to Telerik. The Telerik blog also mentions a 4095 selectors per file limit.