#1 rule to stay out of jail by thegrugq: stop talking
It is the classic mafia problem. Yes you can make lots of money on the black market, but it is useless if spending means getting caught. Hence money laundering.
I bet he raised the money through a group loan, fund or he runs a coin mixing service/mining pool. something that would give you expertise in setting up secure wallets. This is why saying anything is bad unless it's for misinformation only.
DPR clearly hasn't seen the weev court docs where everything he wrote on IRC was used against him to cement a flimsy case
Failing that go looking for hosting services that accept bitcoin, or online wallet services esp one's coded in php, since this guy has expertise in that area it's logical to assume he's running a hosting front so when the feds come in to seize the servers, he would be the guy they ask to retrieve it. You wouldn't want to trust your multi-million dollar drug site to colocation you'd want to see your server all day and be able to get to it or notice if somebody sabotaged it. He kind of already dropped he had physical control of the server when it crashed once while he was "out of town". Now cash out a lot of your coins and pretend it's for contract services, DDOS, hosting ect. You could also then enjoy plausible deniability, claiming an unknown customer set that site up and it wasn't you. Since your site accepts bitcoins, you have a reason to be using them. All well and good.. unless you talk too much and drop intel on yourself so they can use other circumstantial evidence against you in court.
He would also have to launder and sell all those coins. If I were him I'd be selling them directly to buyers in an underserved country using a decoy clearnet fixed-rate exchange, or I'd also be running my own small exchange and dumping coins in it, using fake ID scans and paying for traffic to simulate customer records. I'd probably also run my own mixing service like bitfog, lending service, or online casino/betting site to help launder them. If there's any large bitcoin investment funds still around I'd be all over that too, getting new coins out from other investors and giving them my SR coins.
Feds can identify the operators of all the above and then compare them to identity markings DPR has dropped on himself. Anybody with a 60% or higher chance of fitting the profile mark them for long term surveillance they will slip up eventually. Feds already know all of this.. which is why you need to be incredibly careful and never get too comfortable running the world's biggest outlaw darkmarket. Satoshi is a good example of excellent OPSEC. Never once did he stray from the topic of development of bitcoin. There is only 1 post in his entire bitcointalk history that does and it was when he chastised some idiots who wanted to sign up Wikileaks back in 2010 for donations, warning them Bitcoin would be killed before it could even start. He certainly didn't talk about politics with the exception of his genesis block comment. He also seemed to have had chosen a fictitious personality and slid in and out of it confusing anybody trying to go after him. Every unique phrase or word he wrote was analyzed then looked for in old whitepapers and mailing lists... nothing.
He also doesn't give interviews
You would not want to run a heavily used hidden service that you want to remain hidden right beside an exit node. That would be foolish.
All of this kind of stuff would impair site reliability. IMO, if SR went down more often, I'd have a higher opinion of the paranoid exhibited by the admins. A highly reliable underground site is usually either 1) run by people who are going to get caught or 2) run by people who are doing the catching. There's I guess 3) run by really exceptional people who are doing it as a political statement -- generally unlikely, but in this case, possible.
Unless he's DPR.