As a result various releases of v2 were buggy. Capistrano is a hard to test application agreed but its test coverage is plainly woeful.
About 6 months back when 2.4.12 release was broken (https://github.com/capistrano/capistrano/issues/434) I suggested to remove asset pre-compilation stuff from Capistrano. Capistrano is a general purpose tool, company where I work we use it for deploying java, php, ruby and all sort of stuff. I don't understand why it should have poorly tested asset pre-compilation things built in.
I don't know what made Lee work on a rewrite. I can only imagine how difficult it must have been for him to work on something so big singlehandedly while running a company.
His last point is very valid about using RVM, rbenv etc in production. I don't know why people do that. Does that make it easier? Aren't people aware of something like - https://launchpad.net/~brightbox/+archive/ruby-ng ?