I kind of disagree with the statements about running multiple projects at once. I think there are ways to manage many sites and still be very successful in the long run. Based on my experience with website management, it is better to stick to 1-3 primary projects at once (similar to what is said above in another post), but running multiple other smaller sites can never hurt so long as you do not spread your main revenue sources too thin. Lets take a look at the following scenario:
You own a website called basketballblog.com, a subject matter that you have a serious passion for and great interest in. You have been running this site for several months, and have developed a pretty good base of traffic for your first REAL attempt at a website (meaning that you are constantly updating it with fresh content, and gaining popularity with incoming links). You are making about $20 a day in revenue on this website for a total of $600 a month, and $7200 a year. It may not be what the big players in Website Management are making, but it is a good start.
You also own another website called tvepisodereview.com, another site that you have a true interest in. You simply post reviews on new television series on a weekly basis, and earn $10 a day for a total of $300 a month, and $3600 a year. You manage your time accordingly to update both of the primary revenue sources on a frequent basis so that you can build them up in SERPS and build up your traffic (and in the long run, potential revenue).
In total, you are making an estimated $10,800 a year off of your first two websites. These figures are purely hypothetical, but should serve the purpose of my argument when I finish.
Using some of the money you have generated off of your websites, you have decided to invest in some new domain names on a hot new topic. Lets pretend that there is a new piece of technology coming out called the "iPod" (yes, I know that this is already a very popular technology, but once again, this is all hypothetical), and you are one of the first people to stumble across it. You immeadiately buy 5 domain names centered around this new technology, and put up some filler content and fresh articles on your domains to put it at the top of the SERPS as no one else has yet to do so.
Using your already built up sites, you start linking to your new domains to get Search Engines to see them. You update these 5 domains with very basic articles maybe once every two weeks, so that you do not spread yourself too thin on your main revenue sources. When the technology becomes more popular, you suddenly have another revenue source. Lets say that all of your new domains in total are generating another $20 a day with minimal traffic (as this technology is just starting to become well known). This is another $7200 a year.
Now you have several options. You can go along with making around $20,000 a year, and keep building up your websites traffic to build more potential revenue, or you can choose to sell one of your websites for some instant cash.
I myself am a fan of keeping a website, and building it up until I have generated a large revenue source, but I know quite a few people who prefer instant gratification.
The General rule of thumb is that you sell your website for 2 years worth of estimated income. That said, you could probably sell all 5 of your new domains for around $15,000 instantly. However, if you knew how big the iPod was going to be in less than a year, chances are that you would hold onto your domain (or kick yourself later for selling it).
There are some upsides to selling a website however. For example, by selling your site, you can get some fast cash to invest in other websites. I have a good friend who has sold several websites in the past year for over $50,000 a pop, but then again, if he had held onto these sites, he would have definately generated more income in the long run. He continues to prove his method effective however, as he always builds up new websites in a matter of days, which he is able to put a market value on in less than a month.
So in short, yes, it is possible to pay the bills if you really are interested in taking up a career in webmastering
As far as going to college, yes, of course it will help in some ways. I think College is very important, although I am still working on High School, but I do not believe that it is necessary to go to college to run a successful website. However, there is nothing about going to college that could hurt you in the long run. It will help you get more people to hire you for services which is always a good way of earning extra income, and probably open your eyes to some new concepts that you will not develop by yourself.