All of this sounds a lot like my experiences. On the whole, I'd lay out my conclusions like this:

1. Common Lisp is incredibly powerful, but you'll have to write most infrastructure yourself (to be fair; lisp does make it pretty easy to do that).

2. Ruby with Rails is great but you'll have to take the "enforced" structure with it (which is pretty good) or you'll end up at point 1, except that CL really is a more flexible language than Ruby. Neither CL or Ruby extensions are well documented in general compared to CPAN.

3. Perl with DBIx::Class / Class::DBI and a couple of good mod_perl controller classes will give you a good start, but you'll have to choose a bunch of good CPAN modules to provide for the base of your project. Forget about integrated solutions, but the documentation is good.