Why not get managed hosting instead of a dedicated server? You'll pay more, but if your website is worth anything then it will be more than worth it. I can work my way around Linux, even install and configure Apache, but there's no amount of money worth being the guy that gets the call at 6am saying "the site's down" and trying to figure out something like I've seen sys admins figure out (e.g. not enough file descriptors). There's a reason sys admins get paid a real salary. And a good managed hosting company will offer support that you can learn from. If you find it's a peice of cake in a few months then get yourself a dedicated server at that time.