yes of course your site will be penalized if you're referring on making web 2.0 properties and using the same content over and over.
If your building links by creating web2.0 properties and posting articles on it with outbound lins pointing to your site, then I suggest you curate topics for you to post on your web 2.0 properties, that way all outbound links will look natural as your pointing to popular blogs and also in your site.
Google search engine become striker day by day and Google Panda and Penguin hit more and more website ranking because of that when you using one Article at once than become good for long term stable ranking.
Posting a single article or content can be done multiple times by submitting it to different article directories. Trick to it is posting it using different keywords so that it can have variance in a way when you post...
Yea, I agree don't use an article more than once, it will be seen as duplicate content. You can get around this by 'spinning' your article or hiring someone to manually re-write your content so it's technically 'unique' in the search engine's eyes, but they may or may not be a waste of your time depending on what you're trying to achieve.
The way the Search Engines are headed, I would focus more on trying to create truly unique and valuable content. If you always create content of value for your readers you'll also make the search engines happy because ultimately that's what they're looking for too. If you focus on value you don't have to worry so much about Google updates. A lot of my sites don't have a ton of content, but the articles they do have are unique and offer valuable content that readers are looking for and so my sites actually benefit from Google updates.
It can be a lot of work researching and writing, so instead maybe hire someone else to do it on outsourcing sites or find people offering their services on forums, it's worth the investment in my opinion.