This has expressed the ideas in my head far better than I could. When I first started to work with Rails in many projects I just dumped all of the gems I wanted to use in my Gemfile. I quickly learned that a simple bundle update could fuck my shit up pretty badly by having gems change APIs, remove features or both.
Since then I always specify the exact versions of my gems or in cases where the gem authors are known to be comptent use the "~>" operator. I find it to be stupid though much like the article states, why are newer versions making my life harder when they are supposed to be better?