Short bio: Computer Scientist, FOSS supporter (read more)
Tux Machines (TM)-specific
The concept of a rolling distribution is that there are no new releases. You install the base and from there you just keep your packages updated. Before I moved to Gentoo which is my current favorite distribution I was primarily a Slackware user.
After wiping my drive I started the installation which went very smoothly. For the first day I spent a lot of time reading about portage and learning my way around Gentoo. After the first week I was more than comfortable with it. The most exciting part of it for me was being able to keep my system update to date and built the way I want with little effort. Packages built for traditional distributions are precompiled and built against libraries and feature the developers of the distro have chosen.