Currently Being ModeratedFeb 23, 2012 7:57 PM (in response to djconundrum)
This issue seems to have resolved itself. A few days after I posted this question, the larger files started playing over 3G. So odd...
Currently Being ModeratedFeb 24, 2012 5:12 AM (in response to djconundrum)
Keep in mind that iTunes Match will not download tracks over 20MB while on 3G since iTunes Match downloads the tracks as they play as is not a streaming service.
Currently Being ModeratedFeb 24, 2012 9:31 PM (in response to TooDarkPark)
So weird, because now it's letting me. I even confirmed I was on 3G and I'm starting a ~110mb track that had the cloud icon. I guess it's a good problem to have!
Currently Being ModeratedFeb 25, 2012 9:14 AM (in response to djconundrum)
Maybe they have changed the limit with iTunes Match. All I know is back in October, trying to download a large Led Zeppelin song would not work and the song would be skipped and the next one would download.
Glad you got it working.