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Hey, I do blogs, dunno about your windows server though and I wouldn't use anything but WordPress. There are eleventy-zillion spam blogs out there and no way to get traffic to them, so I wouldn't go that route. One, two, three, maybe four tightly-niched blogs, with daily updates, hand written, that will still get you links, organic traffic, ultimately some search engine, and some sales.
Will it be enough to replace a job? I'm not sure -- it's really slow (like, YEARS) to build the kind of traffic numbers to generate the kind of revenue you need. And you need to be creative with revenue models, too. Subscription model is down all over, which is hard on affiliates; you'll want to mix it up if you can, selling something that can't be bit torrented for free.
If you go the blogging route, you'll *need* to find creative ways to get attention and traffic. "Build it and wait for Google" just won't cut it any more.
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