Brian, have a look at the Dunks site, its got a full classifieds section, user profile section, ability to private message, full banner management, and even a 'live chatroom'. Its not as pretty as it should have been as I was under a serious time constraint due to previous web developer letting the domain slide but I think it pretty much does what this site does and more. I run a web development company with 9 staff (i'm not a free lancer) so pretty confident that I'll be around in that capacity for a while, I also built www.kartsuperstore.co.uk as an experiment in creating a full 'copy' of ebay.
As for 'learning' how to maintain the site, the systems I use are fully cms based and really intuitive, but more than happy to provide training and just be there incase I'm needed in the future. I'll give the guys a ring in a few days (got a major pitch to prepare for on friday) and see if they want some help.
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