For that, you need influential groups that can benefit from changing the status quo. In a country that has been suffering from decades of corruption, the elites are generally so widely despised by the population that they have to fear to be imprisoned at best and executed at worst, were they to lose power.
It's even worse in countries like the Lebanon, Syria, Yemen or former Yugoslavian member states, where religion, ethnic disputes and sometimes hundreds of years worth of land disputes and squabbles come into the mix.
I don't exactly disagree, but this is why it can make sense to pursue basic state-building ("good government") and liberalization (respect for basic rights and freedoms) well before worrying about electoral democracy, or a transfer of power away from current policy makers. In practice, the latter is essentially useless without the former - but in the long run, more freedom opens up opportunities for more democracy.
These things only matter in the short run but successful, enduring democratization is a very long game. Look at Taiwan and South Korea - relatively straightforward when looking at them from the outside, and yet they took decades to become stable democracies with real respect for fundamental rights. More challenging cases might take generations.
> Most freedom movements need some form of support from the outside, be it arms, money, logistic or ideologic support.
Most often, the needed support can come from the inside, as influential groups within the country start supporting a peaceful transition to liberal democracy. Arguably, this is even the best possible case.