> A lot of people say that "we should have made a revolution", what they mean is that the "free", externally imposed peaceful transition may not have been the best thing in the long run.

I think you are concentrating on the wrong word: "peaceful" instead of "external". A revolution need not be violent, and either way it implies that there is a real chance a sufficient percentage of citizens is ready to move on from the current system although both violent and peaceful revolutions are prone to slipping back toward the old system or some other form of authoritarianism, for different reasons: violence also attracts the wrong elements whether in itself or as opportunists whereas a peaceful transition may not be able to remove all the remnants of the old system.

The fundamental idea, though, is that the society needs to be ready and willing to change internally. In a way, as much as it infantilizes people, when most of a nation has grown up with a powerful authority, it is hard if not impossible to go straight to relative liberty. Part of it is cultural, part of it is the seeming evolutionary human trait of being either submissive (most people) or dominant (few people). It takes some time for a submissive person to learn to fend for themselves, and as we see with "highly developed" societies today, many are still highly susceptible to needing leaders.

Of the famous recentish revolutions, it should for example be remembered that Marx stipulated the "communist revolution" should happen in the highly industrialised nations (ill-advised as the idea of armed revolution is). Russia in particular, a backwards agrarian empire, was about the last place he thought would be ready for it. And turned out he was right.

Edit: clarified wording of drawbacks of violent/peaceful revolutions.