3- It fails badly when asdf itself is so broken that it can't load asdf-tools. I only very recently (January 2016) modified the lisp scripting infrastructure to build an executable ./build/asdf-tools the first time they are called, hopefully with a stable working asdf.
isn't this a standard bootstrapping issue?
and the usual way to resolve that is to use git to check out the latest stable version into a tmp dir, build the tool, and then use the freshly built tool to test the bleeding edge.
for reference gambit scheme has a sophisticated method set up for adding new features that are then used in the compiler implementation in version n+1.