It is noteworthy that this was created by Phusion, the same people who created Phusion Passenger (mod_rails) and Ruby Enterprise Edition. Basically, a company that really enjoys solving high-profile problems related to Ruby. (First, Rails is a pain to deploy. Then, Ruby is a memory hog in web-application applications. Now, Debian hates RubyGems.) From my perspective, their work is high-quality, and increases my confidence in this 'product'.
I personally wouldn't pay because I'd be surprised if there wasn't a similar community effort very soon, as there is for Python modules and Java classes.
Better for the company to market themselves with - create their own repo, but Open Source it and make sure their URL appear in every aptitude run.
From an Operations standpoint, having two conflicting package management systems is a huge headache. It's one more point of failure on production systems. The jpackage project was a similar effort which packaged oft-used Java libraries in RPM format.
Why use Debian stable at all? Because people trust Debian's rigorous test and release process. Now let's mix your rock-solid Debian system with an external paid-for service the community has no control over...
Interesting... I've been trying to build my servers lately with Ruby Enterprise Edition as the only ruby (a little tricky, since you need ruby to install REE) to avoid the confusion of multiple rubies with multiple rubygem installs.
I wonder how this would work with a ruby install other than the standard ubuntu ruby package.
In the long term we plan om providing an REE package which replaces the one provided by Debian. By then we'll also offer DebGem repositories with packages compiled against REE.