You could conceivably put together a Selenium script or something to automate the first part, but that would be really tricky. As it is, you just have to get an export of your domains (instructions in the repos) and run my script. Right now it supports DNSimple and Namecheap, but I'm almost done with Gandi support and might be adding others.
Transferring domains is fairly painless already, but one click transfer would be insanity. The few speedbumps that do exist when transferring exist to prevent domain name hijacking. If you could one-click transfer then domains would be completely unsafe against hijacking.