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Some time back I was looking for a semi-pro ad server, something that went just a little step further than PHPAdsNew, MaxMedia, etc... Not easy, they where either short of functionality, a phpadsnew variant or way above my budget. After some time browsing around i found AdvertisementManager.com It's a commercial piece of software but fairly priced. It comes packed with features for every kind of ad type you want to serve, from Adsense text style ads to advanced rich media, more invocation methodes than other free solutions and also includes 2 interface modules for either direct PayPal or 2CO processing. I have tried their support on two occasions and it was excellent each time. Installation and operation is very easy, documentation is ok. There are one or two things about more advanced use not in the docs but support quickly responded on my e-mails.
Inside the userinterface things can look a bit "lame" but it works good because it's so simple, anyway many things can be customized, e.g. colors, layout, fonts, etc...
I really whish more ppl would support and buy their product so things can evlove further. No secret I really like this server, but I don't get a dime promoting it.