To be honest, using Web 2.0 links in this way is viewed as a low quality activity. Many of these types of links were targeted by multiple Penguin updates, and too many of them could cause you a penalty.
I'm not saying that all 2.0 links are bad - they certainly aren't. But spammers try to build 100's of 1000's of these types of links on throw-away blogger and WordPress blogs that add very little value to the web. These are the links Google tries to sniff out, so it's best to avoid them. A network of these types of links is Google's very definition of "unnatural" and could quickly lead to a loss of rankings and traffic.
Put simply, Google wants you to earn your links.
To answer your question more directly, the first link from any domain tends to count more than other links. So 100's of links from the same domain don't add as much value after the first links. And yes, this can start to look fishy.
It's best to use 2.0 links in moderation, and make sure you are targeting high authority, well trusted sites. I recommend building profiles on good sites and earning links through adding value.