[Wine] ipod software

[kotton]

i'm new to linux but am an experienced windows user (former ;-) under windows i used a program called Anapod Explorer to manage my ipod nano. it was great. i looked just like windows explorer and all i had to do was drag and drop from folders to my ipod to transfer music. very simple and easy to use. i've looked a few ipod software programs under linux, but nothing comes close to Anapod. i haven't tried to install it in wine yet for fear of stuffing something up with the system. do you think it is safe to try and install programs on linux and wine when they have not been tested? or is that something for more experienced linux users?
thanks