I have very few issues with Ruby as a language, in general it let's me get from thought to working code quicker than any other language I've used. Honestly the largest issues I've run into with Ruby typically deal with people trying to be too clever.
Ruby certainly provides a lot of ways for people who want to look incredibly clever to hang themselves and anyone using their code. I typically avoid libraries or frameworks where clever code is the norm (I'm looking at you Rails), and because of this I tend not to have too many problems.
It's certainly not perfect, and I've been frustrated by bad error messages, stupid type system mistakes, etc. But I've found that those issues simply replace issues in other languages.
I still feel that Ruby gets me from Thought to Code quicker, and for the kind of projects I typically do, that's worth dodging a couple of warts.