The first had me go through a near complete understanding of git, followed by vagrant and then docker. What would previously take me a full day to do (that too with possible mistakes) now takes me just an hour (depending on download speeds) on a fresh wibdows machine. I carry everything I need in a folder on my pen drive. This includes installations for virtual box, vim, cygwin (and its packages), and the config files: vimrc, minttyrc, vagrantfile, and dockerfile. The best part, I know it will work.
As for documentation, the art of it is simple. Read Every Word, Follow Every Example. Simple but difficult to practice. Doing this means disciplining yourself to switch off distractions, being patient to read through the mundane examples because the mundane can hold the most important details sometimes like why a flag works the way it does. Reading documentation is something that takes practice and I've now come to a point where if I have two libraries that serve the same purpose, I pick the better tested and better documented one (tests are a great starting point for source code readings).