Chosen Solution

Flashes Cannot Detect. It will charge when plugged in with USB charger, Then it plays on the Sony but not charge.

It won’t charge but plays on it sounds like the dock connector has either a short or a couple of bend pins. If you can, look closely and see if you notice any of that. Also, spray a few puffs of canned air or similar in it to remove any debris that may be preventing it from making contact. Do the same on the iPod as well. This could be the cause for not being detected and thus not being charged. Should that not work you may have to disassemble the Sony and check around connector CN602. Download the service manual for the Sony from here to work on it. Let us know what you find.