I finally jumped in and have actually had a few pleasant surprised. First, I thought that it would default to the credit card I had on my account. Wrong! I had an existing credit remaining from an iTunes card and it used that. Awesome, it didn't come out of my pocket, at least not directly! I'm thinking that maybe that happened for me because I do have a credit card on file with them and am not just trying to use an iTunes card for my subscription.
Next, I actually have less songs in my library than I thought. I started the process and then once it sorted, I looked at the bottom of my library and had some old college lectures and a few other things that I deleted. I ended up only having 6805 and not 8 or 9k like I originally suspected. So far, so good! It has already gathered info and is almost through matching. I only have 5 tracks that have feel labeled as ineligible. Two are digital booklets, which of course I knew, but the other 3 are just really random. One is Silent Night sung by Sarah Brightman which was an iTunes single of the week at Starbucks last Christmas season, one is The Chicken Dance, and one is Mack the Knife (like I said, totally random, but no problems really). I only have 16 duplicates and I thought I would have more because I am not super anal about my library.
Now I'm just waiting for it to finish, there's about 500 songs left to finish but unfortunately I have to leave. I was hoping to at least get to the point of seeing how many had to upload before leaving. Oh, well!
Anyway, after all the reading and research that I have done to anticipate any problems, I have to say that I am happy. I will probably wait until tomorrow so I can be sure everything is finished before turning it on at work, but my ultimate goal is to be able to listen on my computer at work. For me, this is going to be a great service, unless something really bad happens with my library in the next few minutes. LOL! I guess everyone is different, but so far, so good, and I love it!
Edit: So now it's finished and it is only uploading 894 items. Out of close to 7k, I think that's pretty dang good! Plus, I know about 500 of those are from community band CDs, so I knew they wouldn't be matched. Anyway, now that I'm all matched, I'm outta here! Hopefully some of you that are having trouble get things worked out, it really does seem like a great service!