It bears repeating explicitly I think: you're not working against today's analysis tools, you're working against whatever analysis tools exist far into the future, since everything is recorded for eternity.
From what I've seen, success in this industry is predicated upon planning, caution, and constantly thinking of ways that people are going to screw you over.
If your first thought when making decisions was "what won't send me to prison" you probably wouldn't be engaging in criminal enterprise in the first place.
Most people who break the law do so because they either don't consider the consequences or accept the rewards as justifying the risks. And plenty of criminals go to prison because they judged wrong. That those who are successful for long periods of time buck this trend is just survivor bias.
Well, it's true that the official manual contains mostly short-term, actionable recommendations, but some of them do have the goal of avoiding long-term consequences.
These can be changed and you can be charged under other crimes which may have different statue of limitations. When the government decides they want you in prison, it doesn't particularly care how it does so. Tax evasion, drug trafficking, funding terrorism, CSA changes, weapons smuggling, or RICO or country equivalent, they'll use which ever seems easiest to get you.
For a buyer, this isn't as big of a deal because you won't have that level of target on your back, but for anyone running a marketplace I don't think statute of limitations will protect you once they figure out who you are.