It certainly is great to be able to jump right into Crystal coming from Ruby. It isn't very hard to convert most Ruby code to Crystal -- you just have to go through and "typify" everything. A few methods have different names and of course some don't exist but most of it is there.
My one grip with Crystal however, and why I haven't adopted it more generally, is that much of the "Lisp-like" features of Ruby are all but lost. Crystal makes up for some of this with macros, but it doesn't quite cut it. For example, you can't splat an array into a lambda in Crystal. Arguments have to be tuples which are compile-time bound. Little things like this feel very limiting to an experienced Ruby developer.