I'll use a classic skin if there is one that matches the VS I am using at the time. Someone converted heylove's areao4 in black from XP to win7 and I'm using it but wish there was a winamp to go with it.
For the past 12 years the only media player I've used is Winamp and the only category of skins I've used is Classic. Modern skins never clicked with me. My skin of choice for the past 5 years is this [link]
I also don't use classic skins. At the moment I'm using the Bento skin because it's very practical many custom skins are hard to use even though they look nice. But if I saw something nice from you then I'd gladly use it .
If you decide to take another look to customization, I would be in euphory. Its being mentioned that winamp classic skins had died over the time, but there are lots of media players to choose from. AIMP has many things common with winamp but with easire ability to customization. Foobar is more like a winamp modern or WMP, but also highly customizable. But to the case.. if you want to rip again to Winamp classics, I wouldnt even hestitate to run it again.