Living somewhere else would be a minor hurdle. SR was an international site. Even without an extradition treaty, the feds would go to the country, say "psst, wanna hit a major international drug dealer?" And local police could bust him, jail him, then deport him, and then the USG could try him too.
If your opsec relies on you laughing from some small country, hoping legal barriers prevent your capture, you've totally failed.
Edit: He should have panicked as soon as agents visited him, but I guess he probably talked himself down. Probably figured "well they already have me or they don't", which, was probably true.
The key question for me is still: how did the FBI locate the Silk Road hidden service servers? They never disclose how that was accomplished. If they had an assist from the NSA in breaking Tor, I would like to know. It has been shown that Tor hidden services are not anywhere near as secure as they are thought to be... but has anyone done a practical attack in the wild? Enquiring minds want to know!
Edit: looks like he did move after the feds showed up. http://www.forbes.com/sites/ryanmac/2013/10/09/living-with-r...
I find it VERY odd how they mention they imaged the server with zero information on how they found it. Smells very funny, like they intentionally left that part out. If it was a simple "we asked Rackspace for files on a one Ross Ulbricht" then they'd have said so.
OTOH, they may want us to think it was a secret attack, when it was just more of DPR's poor opsec. If he ordered fake IDs to hire servers but with his real picture... who knows.
I think it'd be hard to become a citizen of a country that has nice imprisonment terms, is where you want to live, and will ensure you're only tried once and never extradited.
Long-term, the best strategy probably would have been to launder the money[1], then become a large donor/philanthropist and get lots of political friends and great lawfirm on retainer. That way if they do catch up to him he's in a better position to deal with the DoJ.
1: Yes, I know, a non-trivial endeavor.