FWIW I ended up buying Anapod. I use Windows Media 10 to manage my library and Anapod to move music to and from the device. I bought it straight away because I read comments that activating the trial version was challenging to some. I paid $30 for the universal version which should allow my wife to activate her Nano and Mini onder the same Household license as well.

It took me less than 5 min after download to get my first test song onto the Nano, however it is not exactly the best documented software. I had never used an Ipod or mp3 or Win Media to manage any media files before.

It seems as if Anapod would work to manage my mp3s much the same way that WM 10 does however I like the WM gui better. There are some features in Anapod such as downsampling that may prove useful in the future, however right now it is simply a $30 solution to get my music on and off my Ipod without EVER installing the iTunes software.

A main drawback for some may be that Anapod will function only when connected to the internet due to required authentication, however this doesn't seem like a big deal to me because:

1) My music only lives on my Ipod and external HDD at home. No need to load tunes when there is no internet connection.

2) I am a load it and for get it type guy. I do not change the music on my Ipod all the time.

Cheers,

Scho