ITunes Plus Upgrade--No help from iTunes Support

Question

I appologize for this lengthy post. Believe me I have more to the story, but want to keep it as short as possible. Bottom line is I'm looking for help with iTunes plus upgrade please.
My specific problem is getting customer support to upgrade my old iTunes songs iTunes to iTunes plus so I can use them on our new Sonos player. It’s now been almost a week since this issue arose and there has been no help in getting my problems solved. My main problem is that there is no telephone customer support for iTunes. All of the support for iTunes is now done online through emails. That is a huge issue in my mind, but not the purpose for this post.
Here is my problem..
I have two iTunes accounts. Account # 1 was my primary account until 2008/09 time frame when I switched from a PC to Macbook Pro. I have 314 songs from 2006-08 that were purchased on Account #1 that I'm trying to upgrade to iTunes Plus. Account #2 is now my primary iTunes account. The Account #2 songs are all iTunes plus and do not need upgrading. I now have all the purchases from both accounts on my Mac Mini serving as a HTC, but the old iTunes DRM songs cannot be played on Sonos until they get upgraded.
My issue solely relates to my old songs on Account #1. I have been trying to upgrade my account 1 songs since last Thursday. My iTunes store account is currently logged into Account 1 when attempting the updgrade. When I first made the purchase, I got the on screen message that I’d get an email with instructions to complete the purchase. Well three days passed and I never got the email. I also noticed that my purchase of $104 showed up as three “pending” credit card charges on my bank account records. This seemed odd so I called Apple for help. Big mistake!!!!!
When I attempted to call Apple Support I was continually given to “technical support” for either my Macbook or Mac Mini. They never listened to what I was saying. In fact one rep told me I would need to pay the $39 fee for technical support on my issue!!!! Finally, after speaking to three different individuals one of the “tech support” reps was able to contact an iTunes support rep. Note, that I could not speak to them, rather it was strictly apple employee to apple employee. I was placed on hold for thirty minutes while they worked on my issue. After thirty minutes I was told to go to the iTunes store and start over. I went to iTunes store and completed the purchase again. Shortly thereafter, I received an email response from iTunes saying:
Dear Tom,
Your iTunes Plus music upgrade could not be successfully completed because there was a problem with one of the items that was to be upgraded. Please return to your Upgrade My Library page and click Buy and your upgrade should be processed successfully. We are sorry for the inconvenience and appreciate your business.
Sincerely,
iTunes Store Team
Based on this email. I went to iTunes store again and tried the purchase….again. I then got the same email response a short time later. I have attempted two other times to buy the upgrades but got no email responses at all. Late Sunday, I called Apple again and also used their online iTunes support page. I got one response late Sunday evening asking a question about error messages, I answered their question by providing them the above iTunes notice. That email late Sunday night was the last communication I've recieved from iTunes support. It’s now three days later and I’m still waiting to hear back from someone at iTunes support. All I want to do is spend 104 dollars to upgrade my 300+ songs, but no one at Apple seems to care.
I am really disappointed in Apple’s customer service. I’ve been a fan of Apple for quite some time, between my wife and I, we have 6 Apple products in our home. The lack of customer support is really disgraceful.
Anyone have any ideas.

Answer 1

This is a follow up. Finally, after almost 72 hours, I recieved another email from the original iTunes support representative. According to her, the problem is that one or more of my songs on the account are either not eligible for the upgrade or the file is corrupted and can not be upgraded. In short I cannot use the "Buy All" feature because I will always hit this roadblock. The only way to resolve this, is to upgrade each song individually or select a few songs at a time to upgrade.
I will have to do this until I get the song or songs that is causing the problem. Once I have identified the song(s), I can chose to repurchase them and get a refund. All songs today are at the DRM free format so repurchased songs will automatically be the upgraded file.
So I'll now begin the upgrade of the 314 songs. I guess it could be worse.
Okay, I got an answer and an offer of a refund, but this answer certainly could have been provided three days ago. Am I being unreasonable?