Wow, a lot of great and interesting replies, way to go!
James, I relate to pretty much everything you said and your idea behind asset organization makes total sense, I guess that's something that I've also been working for the last couple of years is this idea of 'future proofing' any kind of organization method so that it can adopt any inevitable changes later on. And regarding asset location, in our office we're using Deadline which collects and stores all the auxiliary files and assets for every single render on a separate folder (takes up quite a bit of space but is very useful). So that has never been an issue. A bigger issue is re-using assets from old projects but instead of having a coherent library with nice previews, it's always the same process of opening old scenes and trying to find it, copying it and merging into a new project. But I guess that just requires some dedication and time, and I'm sure it will be solved :)
But the main point from all of the above is not to be too hard on yourself regardless of what you choose to do. Life's short. Enjoy it. As long as I can pay my bills and feed and cloth my kids, then I'm happy with all of my other choices.
I really love this kind of attitude too. I definitely find myself putting too much stress on being productive all the time which results in me being not productive at all and then guilt tripping myself even more. Life's short, let's enjoy it :) And I'll check out the book!
And it's always nice to hear anything from your point of view Juraj. I'm also on the same boat with CommonPoint tutorials which I have started but find it difficult to finish it (even though it's so well laid out and all). The amount of information and tutorials out there is becoming so vast that at some point you even start to wonder if it's even worth learning it if you can't learn it all.