I've done Ruby for about 7 years and can tell you that after a while, things fall in place, including (most of) the syntax. For me, the most annoying thing is trying to create and pass around functions -- the syntax for that just isn't as easy as in CL or even Python. Having first class functions and a good function-passing syntax would be a nice addition to Ruby 2.0.
But yeah, marketability notwithstanding, I slightly favor Lisp.