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While I usually encourage people to dig their fingers into the fundamentals of computers in general and operating systems in particular, you should consider the effort needed for maintaining a normal web site: you will need a web server (that's easy: Apache), a platform running your software (PHP, Java,...), a database (MySQL, Postgresql, ...) and the software itself. You will have to think about a backup strategy, set up your own e-mail service (sendmail is a beast!) and spend most of your day thinking about security. The rest you will be busy fighting e-mail spam. You will learn a lot of stuff, but I'd recommend starting with a (virtual) box at home and get your feet wet with the intricacies of Linux. Allow yourself at least a year for this.
(Disclaimer: I'm a systems administrator and responsible for a couple of Windows and Linux servers.)
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