I am in a similar situation with a Win Vista machine I have owned for 10 years, but which I will substitute for another Win machine but with Win10. I have always used Itunes for Win, with excellent results, although in an old state, with Itunes 10.1 from 2010, version with which I stalled in 2010 because I didn't like what was coming next. Specially sightwise.
Now I am in a situation where i'm going to change to the new machine (maybe tomorrow), but I don't want to lose my whole library, which is more than 61 Gb big. I assume I'll have to install the latest version of Itunes because mine doesn't work in some things anymore. Like for example updating podcasts, where I always get a Couldn't establish a network connection message, although there IS that connection. So how is Sharepod? I'm not particularly worried about Ipod compatibility, because though I had one, I don't use it anymore.