But as touched on, the real question is how well does disinformation work against LE? We see all sorts of dumb reveals in court documents. A single line like "yeah I spent 30 days in jail for pot last summer" really narrows it down. But how far will it throw LE off if such a slip is false? Are they actively trying to determine this kinda thing? Without knowing how many investigations simply fail, I suppose it's hard to know.
I guess the best indicators are the long-standing evasions we know of, such as the FBI agents that the KGB turned.
The other take-home lesson is to use high-latency communication. In the lulzsec investigations, agents monitored when Tor was on in the suspect's apartment, correlated to when the handle was chatting. (OK he was probably toast at that point anyways.) I'd also guess that doing batch communication reduces the tendency to slip up. No small talk. Also no external interruptions ("sorry, power just went out for a minute") to mention.