Some playlists and/or songs "not eligible for iCloud"

I have a playlist that contains only music but iTunes Match refuses to upload it, saying it contains "other media types".
Having thoroughly gone through the contents of the playlist, I have found one song, a Frank Sinatra .mp3 ripped from a CD I own, that is listed as "not eligible for iCloud", as well as 4 songs marked by iCloud as "duplicates"
I have tried manually adding the Frank song to iCloud but its status remains unchanged.
The song, in mono, is a 733K MP3
I had to convert it to AAC which nearly quadrupled the size of the file to 3.2 MB and now it's uploaded...
However the status of the playlist remained unchanged until I also removed the "duplicates"
a) iCloud should nevertheless sync playlists, minus the ineligible tracks
b) or you should get a warning that it won't sync the playlist, and better error reporting so you can actually understand what the issue is, as opposed to the usually vague "iCloud doesn't like your track, but won't tell you why" message...
c) duplicate tracks in playlists should automatically (or after a prompt) be replaced by the original track that is in iCloud.
iTunes Match, you have wasted many hours of my time despite my well organized and healthy library.
Argh.

Resolution
Icon
Description
Definition
Ineligible
This icon is displayed next to items that are not eligible to be uploaded to iCloud via iTunes Match. Some examples are songs that are larger than 200MB or songs encoded at 96 Kbps or less.
Removed
This icon is displayed when a song has been removed from iCloud (from a different computer). Songs deleted from iCloud are immediately deleted from associated iOS devices, but will remain on other associated computers until they are manually deleted.
Error
This icon may be displayed if the song file is corrupt or if there was an error uploading the song. Try updating iTunes Match (Store > Update iTunes Match) to resolve this. If updating does not resolve the issue, try importing a new copy of the song into your iTunes library.
Duplicate
This icon is displayed when a duplicate version of this song exists in your iTunes library on your computer. This icon will be displayed next to duplicates that were not uploaded to iCloud.
Waiting
This icon is displayed when a song is in the process of being matched, but has not yet been processed.

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Sorry, Maybe I didn't explain that correctly.
The song has to be available to purchase in the iTunes Store in order for it to be used in Match.
So if you purchased a song from another source or imported it from a CD it sould show up in Match!
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Some playlists and/or songs "not eligible for iCloud"

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