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If I was to join one today, I think I'd start with the SEs and try to identify which are prominent, well established, and stable. Even if the traffic is limited, one that's listed well should provide a links boost.
Depending on the script you can have a lot of management flexibility. Many rings can be set up to automatically or manually reorganize the order served up (for instance, stagger high and low traffic sites to give a fair chance to all sites in the ring). You can also choose to have as much option in managing as you want (to approve all additions) or let it be free for all who apply.
That said, be aware that the most popular web ring hosting system, webring, is now a wholly absorbed part of Yahoo! If you use them to host your rings, all applicants have to go through a Yahoo! ID to join and manage their end of web ring joining. Which can rather defeat the purpose of bringing them into your site for the web ring activities.
I wonder how search engines view those links on a page? Competition?
For a personal page or human interest page, I wouldn't hesitate to join one - but commercial? I would question it.
I have clients who participate in four different webrings, and they are not a big source of traffic. But the traffic is highly targeted and therefore easy to convert.