@Mikey85: Matt Cutts changes his mind every now and then and in one of the latest videos on the very issue I saw him stating that (beside the "almost thing" tedster mentioned) protecting webmasters against google bowling attacks never has been a priority.
However, my experience on you're questions:
- I am quite positive that automated filters are at place which will drop you for artificial link building patterns (too many, too fast) and anchor text optimization. As those filters are automatically, you can get out automatically, too: Get more links, with other anchor texts, from trusted sites.
I can also say that some really strong sites of mine with a nice backlink profile (a lot of universities link voluntarily to those),do not seem to be vulnerable to such filters and links. It is just new sites (< 1 year) with mainly footer links, free-for-all-site links (squidoo, article marketing, blog comments etc). In those cases even a nofollow link in a squidoo seems to cause trouble after a certain degree of "infractions"