Can you boil your position down to a single question? Even this post raises such diverse issues such as

• .. there is a large number of would-be Perl users that are intimidated by the vast number of (CPAN) options.
• .. in order to get up-and-running with something as simple as a JSON-aware guestbook backend for an AJAX website we have to understand many things:
• .. Ruby and PHP are technically inferior to Perl in several ways, they are very popular with newcomers because they are easy to get started with.
• "Training Wheels Perl"
• Sure, maybe it's just marketing, but I know what I'm doing and it still takes me a few hours to go from a fresh install of CentOS/RHEL/Ubuntu/Fedora/whatever to a working server with the following installed:

Some of these have nothing to do with Perl. Yes, there are many choices on CPAN. So?

And writing a JSON-aware guestbook probably requires you understand what a 500 Internal Server Error is in any web programming language, including PHP and Ruby.

Installing a new server with a bunch of packages takes a while, but are you doing this weekly? And if you are, why not standardize on a set of packages and go with that, updating your standard install quarterly?

I really don't see what problem you're trying to solve.