I've been having this problem for the past week and a half. I finally got one song to match the other day and was happy. I just want a match or an upload, because I want it on my phone. I dont want to have to disable match on my phone just to put my songs on it.
Today (6/3/2012) I have been trying to get an album to upload. I left the room (stuck on "sending to apple") and came back after dinner. When I came back the songs were everywhere, (uploaded, matched) but thats ok, it dosent matter. I tried downloading them on my phone and just got an error with 3/4 the album "Unable to download.etc.. etc...".
I tried encoding the album to AAC 256 since AAC is apparently a lot more friendly with iTunes Match (note ALAC songs not uploading) and I'm trying again. Still stuck on "sending to apple"..
HIGHLY FRUSTRATING.
Oh I also forgot to mention, I have had to put songs onto my phone using goodreader, since again... my library is frozen (as in, stuck with what I have downloaded) on my phone with itunes match being down.