There's only one way to evade law enforcement for a long time, and that isn't it (in fact, it's kind of the opposite). The key is that doing business requires relationships -- very strong or very weak and everywhere in between -- and every relationship can be exploited. The more evasive you persona is, the more elusive, the less business people will be willing to conduct with you. So the more you try to hide, the less business you'll do and your crimes won't pay even without any enforcement involved -- you'll be punishing yourself for very little reward.
The way police thinks is like this: first they'll find someone close to you and try to flip them by exerting pressure (on them or on you). If you don't conduct business with close relationships but with strangers, they'll plant an agent. The more secretive the crowd you hang with, the higher the chances the man on the other end is an agent. If your strategy is that no one knows anything about you, you'll find that you won't be doing much business anyway, and so wouldn't become a police target anyway, and if that's the case, you've gone through a lot of trouble while simply remaining a small fish without any evasion would have been better. So the hiding technique you describe might work for a one-time crime.
The only technique that works for any significant amount of time actually relies on very strong relationships: organized crime. It is a feudal system of patronship and loyalty -- your employees depend on you and they'll be willing to go to jail for you -- combined with a the very powerful stick of physical intimidation, so that people are afraid to snitch on you.
In the case of this Ross, did he really need to cultivate relationships that required personal details leaking? From his story it doesn't seem much of the case. After some initial startup time, people were just winning to trust SR (the stupid ....). The hustle to sell some initial product looks to be the only exception, and yeah, with no risk you might have a hard time starting a business.
The ideas I've outlined would work for more than one person, though I'd be very hesitant to trust others, and you would need to find such candidates in the first place.
Hiring agents should have been taken as a given. You're paying someone a few thousand bucks, and you don't think they're going to sell out if someone comes along that has far more? SR should have been robust to malicious actors. DPR can keep the root level stuff to himself, while allowing his admins to have limited tools. Periodically review stuff.
I fail to see how organized crime would be an option for someone like Ross, wanting to start SR. So while that may be an option for some (a Mafia style threat profile is not something I'd likely be happy with) it's not really that viable for a random startup. I mean, here's another way to be immune from a lot of regulations: be really rich!
Also, when I say persona, I'm referring to the currently active one that you're using at the moment. Silk Road claimed to have been run by a line of these guys. Yet there was no real evidence of that, eh? If multiple personas would have been properly used, we'd see changes on the site, the staff would know, you be wouldn't have old documents, etc. That's what I mean by fully going into a persona. You might use one disposable persona to buy an order or two of bitcoins. Another to run a server. Etc. Anywhere you need to draw a line between one act d another.
The way police thinks is like this: first they'll find someone close to you and try to flip them by exerting pressure (on them or on you). If you don't conduct business with close relationships but with strangers, they'll plant an agent. The more secretive the crowd you hang with, the higher the chances the man on the other end is an agent. If your strategy is that no one knows anything about you, you'll find that you won't be doing much business anyway, and so wouldn't become a police target anyway, and if that's the case, you've gone through a lot of trouble while simply remaining a small fish without any evasion would have been better. So the hiding technique you describe might work for a one-time crime.
The only technique that works for any significant amount of time actually relies on very strong relationships: organized crime. It is a feudal system of patronship and loyalty -- your employees depend on you and they'll be willing to go to jail for you -- combined with a the very powerful stick of physical intimidation, so that people are afraid to snitch on you.