Hey, (I know I'm replying to my own post, but) I now believe I know what's going on and have a solution for others who are similarly affected.
Apparently newer iPod and iPhone models use USB charging circuitry to charge their batteries. Older chargers provided power through the FireWire portion of the connector. My iPhone 2g must have been able to charge via FireWire, whereas my newer iPhone 4 must charge via USB. However, this doesn't explain why it charged on the old dock, before I connected it to the Mac (in order to download my old iPhone 2G music/apps et cetera).
Anyway, some firms have made converters to put between old docks and newer iPhones:
http://www.griffintechnology.com/products/firewire-t...
This particular one has been discontinued, but I've managed to pick up a used one on eBay.
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