No, that doesn't work because Rockboy only saves the gameboy SRAM to a file on disk when you exit it cleanly; the original poster has been hard-resetting the device to get out of the plugin, which doesn't save any data.
There are not enough buttons on an iPod for the menu to be mapped to anything other than hold, you can try changing the keymap yourself and doing a custom build but you'll find it hard to get a different button that doesn't ruin your ability to play games.