This is literally an a question with no specific answer. It all depends on a lot of different factors i.e. market you are in, technology being used etc etc ...
I would try this out with 10 of the best article directories first and see how it goes. A lot of the one way links you gain from submitting to thousands of directories are not that good.
Its not as easy to make money of Adsense as it once was. The web is becoming a lot more competitive and people are paying less attention to ads. Just be warned in case you have ideas of throwing up a blog plastered with Adsense ...
SEO is part of an overall SEM strategy. I think a lot of people think SEO is just about sticking keywords in your page titles, headers etc. But really it's a whole marketing strategy around your website. SEM usually refers to SEO + PPC ...
Good SEO would require some investment up front but once up and running it can be a lot less work to maintain (if done right). I would maybe outsource the initial strategic part of the work but make sure they provide you with a monthly task sheet of things you can do to promote the site yourself.
Thats going to be a hard question for people to answer. Everyone enjoys SEO for their own reasons. I am from an IT background and worked on large web applications. I have always loved the net and online marketing ...
What do you like doing in your spare time ... ?
As someone mentioned there is no real duplicate content penalty, as in Google will not put you in some black hole marked for sites with duplicate content. The problem with your site is, depending on what keyword you are targeting, the sites you take content from will more than likely rank above...
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