Bitcoin Scavenger Hunt Proposal - With Eventual Prizes

[brocktice]

I would like to propose a test of bitcoin's anonymizing properties. The plan is to do two or three 'transactions' with various levels of anonymizing.

Level 1 would be small, say 5 BTC, and would be something simple like sending from one address to another, maybe with one intermediate step.

Level 2 would include some reasonable mixing, say sending between a couple of accounts, and would be probably 10 BTC.

Level 3 would include the best anonymizing steps I can come up with / have suggested from the community, price of 20 BTC.

I would probably use not-quite-even numbers to make the amounts easier to find, as they probably would be in real transactions. The prize would be if you can trace the path of the money, or maybe just find the beginning and end transactions, I'll give it to you.

I'm soliciting feedback on (a) any refinements I should make to the rules/process and (b) the best possible anonymizing steps you can suggest. Once that's all squared away the game will begin. Thanks in advance!

[SgtSpike]

Hmmmm... interesting.  I can think of some out-of-the-box ways to track transactions, to where I could just as easily find the hardest transaction to track as the easiest.  So... Challenge Accepted. 

I assume you would give the starting address and initial BTC amount sent out?  Or... what information would you be giving?