I see you updated the original post.
EclipseMC picked up the 0 fee transaction.
Conclusion: The miner must be using a custom set of rules when picking transactions for this to work. I got really lucky in the practice round.
One big different between your first trial and your second was that the second transaction was under 1K bytes, and the first was something like 2K. So it would make sense that a "spam-like" transaction wouldn't confirm for many hours leaving the opportunity for a mining node with a "higher fee trumps a lower fee" customization to have the chance to mine a block.
I see that in the second trial the "Relayed by IP" is again 127.0.0.1. Had you sent that from Blockchain.info?
Yes I had sent it from blockchain.info. I was considering sending many 0.01 transactions to an address and trying again, but it's a lot of effort (the whole double spending process). I may get around to trying it again tonight. But also something different about the second trial, the payment from satoshidice includes a fee.