Assume that I want to do business with Alice in a hypothetical transaction involving 50BTC. Alice holds an entire slew of addresses, however with enough analysis people will be able to deduce these addresses are Alices because she is well known. I generate a few receiving addresses and have Alice send me these 50 BTC in unequal sized increments at different times. I now hold 50 BTC in say 3 distinct addresses (say holding 17, 20, and 13 BTC respectively). I then generate 5 more receiving addresses and send the BTC to myself from these three at different times in unequal increments. The network sees three addresses that received from the same source send to 5 addresses. Using these 5 addresses I then create more than 5 distinct accounts at the various exchangers. I send these BTC to these say 10 accounts in unequal sized increments at different times. I trade these BTC for digital EUR, USD, SEK or w\e (digital as I do not physically call for cash, I just "sell" the BTC and have cash on my account), let the transaction sit for a day and then buy the BTC back at market rate (I assume I get different BTC). I transfer back to my physical wallet, create new accounts at the exchangers, and repeat the process for as many iterations as needed. I make sure to permute the exchangers in that the BTC I received from GOX will not go back to GOX immediately, it will go to say MyBitcoin. At each step I am generating new addresses, never sending and receiving to the same one. I then finally transfer to my main Mt. Gox account from these various addresses in unequal sized increments at different times to different receiving addresses. I then cash out via Dwolla.
How would one be able to trace my transaction back to Alice without subpoenaing every exchanger that I use? Are there any flaws in my logic? I know nothing is 100% anonymous but is this at least a good obfuscating attempt?
EDIT: I forgot to mention that the various exchangers will be accessed at different times using TOR, creating a new TOR circuit for each connection. The accounts will be created at different times using the same TOR method as well.