The state of Cardassia at the end of DS9 was a broken devastated world. But will this lead to change for the better in their society ( A free democratic one), or will the Cardassians go back to their old tyrannical ways. Or will they even leave their homeworld and become a migratory race. What do nitpickers think their future will be?

Well, from what I read in "A Stitch in Time" they seem to be headed for a much more democratic system based on the Federation, but you have to remember that it is Garak talking....

One would have thought that in that treaty the Founder signed at the end of "What You Leave Behind" were included some reparations for Cardassia. Or, that the federation would come up with a 24th-century Marshall Plan. Germany and Japan had a rough time after WW II but eventually came out with very strong economies because they didn't put any money into their militaries.

What's unclear is whether Cardassia is now occupied territory?

If no aid is forthcoming, I can see a dictatorship. Conditions like that are what leads to demagogues. Not to invoke Godwin, but consider the Weimar Republic in the '20s. The conditions there led to the rise of National Socialism (of course the Depression and the fact that Germany had to pay reparations didn't help either).