In strictly hypothetical terms, I think you're over thinking this. You're doing it all wrong. Stop it. With financial compliance laws in the US, you're going to set off some kind of red flag. Remember, exchanges are required to inform on you for anything that might look suspicious. Don't chance it.
Simply, use a service like Bitplastic.com, and swallow the 5%+1BTC fee. It's essentially a pre-paid MasterCard that works on the coinbase (I think) exchange rate. If you're in the US and doing bad things, this is appealing for a couple of reasons. The first being that it's an international card, so the FBI and local law enforcement has no jurisdiction over it. They would have to call Interpol on you, and they're not going to do that unless you're important. Stay unimportant, and you're made in the shade. The other thing that's nice is the simplicity of it. You don't have to involve an exchange (ie: a second or third potential point of failure) to use your ill gotten wealth.
The other thing I would do is start an LLC out of New Mexico. New Mexico LLC's are great, because they're almost totally anonymous. They're not totally online yet, so it might take a couple of months to file the paperwork. Trust me when I say this: It's totally worth having one of these. Anyway, from there, start a Delaware LLC that is registered to you, and not the New Mexico LLC. Still with me? Make sure both companies have bank accounts with different signers. Funnel the dirty bitcoins into the New Mexico LLC, and have it contract with the Delaware LLC to do some sort of legitimate work. Keep a record of this work. Call it "consulting." Just be careful, so that there are absolutely no ties between the companies on paper. When it's time, have the Delaware LLC pay taxes on all work. At that point, you're legal, only the anonymous LLC is tainted, and you're good to go. A third offshore LLC in a place like England might also be useful, but I don't want to get into that right now.
If you try something like this, and screw it up, you're probably going to prison. Just remember that I take no responsibility for anything you may or may not do with these ideas. On the other hand, this too may be over thinking it. It's been my experience that the simplest solutions are usually the best.