I've been looking at the source codes of some of my competition and many of them have a bunch of link rel=stylesheet... and it links to multiple CSS files. There are like 7 or so and each different file deals with a different aspect for the most part. I'm wondering, is there some sort of SEO behind this or is it just because of the program they used to make their layouts (as I know the two sites I am seeing this on used the same program that automatically did this for them). From my knowledge, I'd say, they are hurting themselves. Am I correct?
They are hurting their users, not themselves. The number of linked stylesheets has no impact on SEO, but it does increase the time it takes to download the page on the first visit. However, once the linked files have been cached by the browser, the download time decreases dramatically. This post I wrote on SitePoint should help explain things for you: http://www.sitepoint.com/forums/showthread.php?p=3975485#post3975485
It doesn't hurt with spiders crawling either? I thought there was some specific reasoning behind using external CSS other than ease of updating your site all at once.