It is possible to change the dock connector on this model but it's not an easy thing to do. A hot air soldering iron is necessary.

It is possible to attach the flex to the board without using special adhesive or tools. I have been successful 100% of the time by simply using no material between the flex conductor and the board pads. I align them up properly and use a small strip of foam on the top. Pressure is applied via the foam when the metal LCD frame is screwed into place. It's most important to clean the residual adhesive from the pads and get the flex aligned properly. I have used 3M command foam and it seems to work well.

Well, you first have to find a replacement dock connector. I order them directly from China on eBay. To remove, you need to disassemble the iPod completely then remove the solder from the two anchors of the dock connector with desoldering braid. I then use a hot air soldering gun to heat up all the pins at once and remove the old connector. I then install the new connector in reverse. It is a delicate process requiring plenty of patience.

I have replaced the dock connector on the 2nd, 3rd and 4th Gen touch. I can help. Let me know if you're interested. It's a very difficult process especially on the 4th that requires special soldering equipment and a microscope.

I have worked on many 2nd generation touches and have had great success in replacing the wifi flex. I have commented about my personal procedure on replacing them in another thread but I avoid using any type of conductive tape or adhesive.