Prodigal_1 is absolutely correct with the diagnosis. However, do NOT order from rapidrepair if you plan on doing the work yourself. Search eBay real quick for "headphone jack ipod video" and pick one up for $3 instead of $40 +shipping. I bought a brand new front and back and new batteries to completely re-do my ipod and my wife's ipod for less than $50. (two brand new ipods pretty much :P) With RapidRepair.com I was looking at spending ~$170.
RapidRepair has good guides, though, on disassembly. There are other guides out there such as ifixit.com and the great google databse. Takes a steady hand, but you can do it.
Just so you know which type of iPod you need parts for, you have a 30 gb fifth generation iPod video. It sounds like your jack is faulty and not getting a good connection. A new jack from an online store is about $40. Just type in iPod parts in your search engine. Rapid Repair is at the top and they will do free diagnostics and they sell parts and have online tutorials showing how to very carefully replace these parts.
Middle round button wont come come out its stuck in?
It could just be old
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