I think the problem here is not about the threadstarter not reading the manual or not, it is about his/her difficulty transferring song into the Shuffle. From his/her post, iTunes bailed out whenever it is clicked, so he/she is looking for other alternatives other than iTunes to get his/her songs into the Shuffle.

Unfortunately though, i think the only way to remedy this is to diagnose why iTunes bailed out when selected. That troubleshooting, only you can do, threadstarter.