Digi-Key, Mouser, RS, and aggregators like Octopart have parametric searches for components; that can narrow down options pretty quickly, so for searching VCEO of a transistor, you wouldn't need to read and understand many datasheets.
Understanding a datasheet is more or less understanding electronics as an engineering field; it's one of many skills an engineer develops over their education and years in the industry. However, it was not a subject that was particularly taught during my Masters' (we did study chart-reading in datasheets but that was about as far as we went.) I can see why some students/young players would find it difficult, I did too. All I can suggest is to start reading datasheets as a habit, for every component you intend to use. If a parameter is unclear, then try to research it or ask on a forum like this. As an single subject, explaining datasheets is quite hard, and I'm not sure your website would really be that much more than explaining electronics theory.
I'd also say writing datasheets is an art - one which many manufacturers get quite badly wrong - though that's another matter.