Actually, Madred never associates the good old days with his youth.
His youth was hell. The military was there to lift him from that hell. There's little data on when the military came to be, though.
The data on the good old days is limited to this:
"Did you know that Cardassia boasts some of the most ancient and splendid ruins in the entire galaxy?"
No data on the age of those ruins, other than the likely interpretation that those place went to ruin in ancient times already.
"I know that the burial vaults of the First Hebitian civilisation are said to be magnificent."
This in response to the "ancient ruins". Apparently, the First Hebitians aren't around any longer. But they clearly didn't live in abject poverty! (Although the young Madreds of their time may have.)
"Apparently when they were first unearthed two hundred years ago, they were. The burial vaults contained unimaginably beautiful artefacts made of jevonite, a rare, breathtaking stone. But most of those objects are gone."
No data on whether the unearthing was by an impoverished and militaristic Cardassia, or perhaps by the spiritualistic and rich Fifth Hebitians.
"What happens to impoverished societies. The tombs were plundered, priceless treasures stolen, a few were preserved in museums but even those were eventually sold in order to pay for our war efforts."
This really sounds as if the society was both impoverished and at war during the unearthing already, and we have no data on how long this state of affairs may have existed. Had the unearthing 200 years bp taken place in the good old days, the riches would have gone to museums first before things went south. Yet Madred says most were stolen right off the bat.
Regardless of whether Madred is 200 years old or not, the days of bliss would seem to be well before his day. And the war would seem to be old news, not an instant cure to poverty but more like one of the contributing causes.
"That war cost you hundreds of thousands of lives. It depleted your food supplies, left your population weakened and miserable and yet you risk another war."
Picard really feels the war was bad for Cardassia. But which war? The Feds haven't been fighting the Union for 200 years, as far as we can tell (but we really can't, because we couldn't during the first half of TNG when the war was ongoing!). Is Picard speaking of some sort of a never-ending sacrifice that characterizes modern Cardassian existence, and has for centuries? Is the Union at constant war?
Probably not, because Picard then speaks of that "another war", as if there currently were none...
Timo Saloniemi