Great post, Vinay.
It’s really an interesting how unexpected variations of content can really break a design.
Another favourite of mine is how really wide or really tall images break lightboxes (see: Facebook).
We have responsive designs for different viewports, but I’m not sure if there are any real responsive design patterns for different content?
Super long words, multi line headlines, extreme image ratios, multiple nestings (think super long comment threads indented by each reply to a point where the comment is no longer readable), counters… all things that help break the careful pixel perfect designs of web products…