There are no simple answers here - genuine democracy with guaranteed political freedoms like you describe can't be imposed from above or from outside, it has to come from within to work, and even when it does work it can still backslide towards authoritarianism as we have seen, in different ways and to different extents, in countries like Tunisia, Turkey, Hungary and perhaps in the near future even the USA.
You mentioned Iran - obviously a textbook case of the revolution against one kind of oppression leading to a different, in many ways worse, kind of oppression. But you know, the 1979 revolution wouldn't have happened if the people at that time had been genuinely free, and the new Islamic Republic wouldn't have been so hostile to the West if the West hadn't tacitly or openly supported the suppression of the Iranian people. If we truly want non-Western countries to fully embrace democracy, full political freedoms and the like, there are no magic shortcuts to achieve that but we'll have to give them the space and time to follow their own paths and make their own mistakes along the way.
I think you just made an argument against sanctioning Israel itself, or even Apartheid South Africa. I'm not saying you're wrong, just that your argument, if correct, probably proves too much.
But I guess generally you agree that a 'free Palestine' is probably going to remain shitty for the newly-'freed', unless they're the ones in power. (And maybe even that those in the West who chant the phrase in question are mostly cynics who don't care overmuch about freedom)
