Would you guys say that due to Wordpress's dominance in the marketplace, that there are more plugins available than there are for SS?
Of course. More developers, plus bigger market, and wordpress has been around much longer (at least as open source). You are much more likely to find tutorials, hosting and modules for WP simply because its so popular but in terms of building modules I've at least found SilverStripe much cleaner and easier to extend with modules.