IMO, Rake was the other killer app for Ruby, but Rails sucked all the oxygen out of the room. It's highly underrated as a both a generic build system and a Make replacement.
Yeah, that's the thought - reduce the friction for converting Python to Crystal. I wouldn't expect many non-trivial programs to work out of the box, but if this tool reduces the time needed to port something, it's served its purpose.
However, it is heavily based on the (abandoned?) py2rb work by Naitoh which I made enhancements to.
IMO, Rubyists should have an easier time with Crystal syntax since it is more similar. Also, the likelihood of having type annotations in Python is much higher than Ruby because type annotations have been around longer in Python, iirc.