What was the last point the Southern Dynasties could reliably defeat the North?

Very few Chinese dynasties have managed to unify China from the South, with the Ming and the ROC being the only examples. However, as I understand, at the start of the Northern and Southern Dynasties, Southern regimes like Liu Yu's Song Dynasty were regularly able to defeat the North; with the situation reversing towards the end of the N&S Dynasties.
  1. What was the last point the South could reliably defeat the North?
  2. Why did the South fall behind the North? I suspect it had something to do with population disparity or scinicization?
 
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I'm not knowledgeable enough to answer number 1, but I think I know one reason for number 2: the south is very mountainous and has a subtropical climate, while the north is more flat and temperate, which makes it easier for wealthier, more centralized states to form.
 
I'm not knowledgeable enough to answer number 1, but I think I know one reason for number 2: the south is very mountainous and has a subtropical climate, while the north is more flat and temperate, which makes it easier for wealthier, more centralized states to form.
But doesn't the south have the ability to support a much larger population given how productive the land was? Take for example the Jiangnan flatlands where most Southern regimes had their political and economic centres. Doesn't that make Southern China in essence a more "compact" power?
 
Very few Chinese dynasties have managed to unify China from the South, with the Ming and the ROC being the only examples. However, as I understand, at the start of the Northern and Southern Dynasties, Southern regimes like Liu Yu's Song Dynasty were regularly able to defeat the North; with the situation reversing towards the end of the N&S Dynasties.
  1. What was the last point the South could reliably defeat the North?
  2. Why did the South fall behind the North? I suspect it had something to do with population disparity or scinicization?
The point when the Southern Liang Dynasty imploded.Prior to Hou Jing's rebellion,the south was actually in a prime position to conquer the North,given that northern China was divided between Western Wei(Northern Zhou) and Eastern Wei(Northern Qi). Hou Jing's rebellion destroyed the economy of the south and the fracture that resulted from this enabled the two Weis to conquer Sichuan and Southern territory north of the Yangtze. The territories the two Weis conquered were the most populated areas of the Southern Dynasty.

Prior to Hou Jing's rebellion,the Liang Dynasty could fight northern armies effectively(one of the largest pitched battles of the period,the Battle of Zhongli,which crippled Northern Wei, was won by Southern forces),and regularly did invade the north.One commander(Chen Qingzhi) was good enough to take advantage of the collapse of Northern Wei and capture the Wei capital with only 7,000 men,but he was not supported by the rest of the Liang army and was soon defeated after being confronted by an overwhelming Wei force.

The main reason why Southern Liang didn't conquer Western and Eastern Wei was because Emperor Wu of Liang(being an usurper himself)did not trust his best commanders,and often entrusted the control of the army to his incompetent relatives. The guy had no trouble finding effective commanders,it's just that he doesn't trust or use them.He only uses them whenever his incompetent relatives were defeated in battle,and the North counter-invades the south. After the North's counter-invasions were defeated however,he just returns command of these armies back to the same incompetent relatives who were defeated earlier.
 
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But doesn't the south have the ability to support a much larger population given how productive the land was? Take for example the Jiangnan flatlands where most Southern regimes had their political and economic centres. Doesn't that make Southern China in essence a more "compact" power?
It’s important to note that during the Northern-Southern Dynasty,much of the south was largely still undeveloped and that the Han population was mostly restricted to parts of Sichuan,Hubei,Zhejiang,and the Wu area.The rest of the empire(Guangdong,Guangxi,Yunan,Hunan,parts of Sichuan,Vietnam and Fujian) was largely inhabited by primitive tribesmen who rebelled periodically.
 
Very few Chinese dynasties have managed to unify China from the South, with the Ming and the ROC being the only examples. However, as I understand, at the start of the Northern and Southern Dynasties, Southern regimes like Liu Yu's Song Dynasty were regularly able to defeat the North; with the situation reversing towards the end of the N&S Dynasties.
  1. What was the last point the South could reliably defeat the North?
  2. Why did the South fall behind the North? I suspect it had something to do with population disparity or scinicization?
Ming unified China more from the Center than the south, the ROC is the same.
The last point for the South to win was probably 1864.

It was in 1864 that the North truly, decisively won against the South with the March to the Sea, even though it took until 1865 for Lee to surrender.

What was Lee thinking, anyway, when he decided to invade the North and besiege the federal capital? Didn't he realize that the legitimate government would soon secure the Grand Canal?
ROFL
 
Then why is the question formulated this way? Both the Ming and ROC are relatively recent unification from the South.
The question was about Southern Dynasties during the Northern-Southern Dynasty period. The Southern Dynasties had the initial advantage in wars against barbarian regimes to the north and were able to conduct massive offensives with varying success. Yet,the period ended with the Northern Dynasty(Sui Dynasty) unifying China.
 
It’s important to note that during the Northern-Southern Dynasty,much of the south was largely still undeveloped and that the Han population was mostly restricted to parts of Sichuan,Hubei,Zhejiang,and the Wu area.The rest of the empire(Guangdong,Guangxi,Yunan,Hunan,parts of Sichuan,Vietnam and Fujian) was largely inhabited by primitive tribesmen who rebelled periodically.
Yeah, I knew that. But the Jiangnan region was quite well-settled, no? Could the region compete with the North China Plain in terms of agricultural output?
The Southern Dynasties had the initial advantage in wars against barbarian regimes to the north and were able to conduct massive offensives with varying success.
What was this advantage? I'm guessing technological or organization?
 
Yeah, I knew that. But the Jiangnan region was quite well-settled, no? Could the region compete with the North China Plain in terms of agricultural output?

What was this advantage? I'm guessing technological or organization?
Organization of the state.Due to the massive chaos in the north by various barbarian groups,there was not a lot of state organization.A lot of counties did not even have magistrates.By the time of the Northern Wei Dynasty,the dust settled and centralized government was slowly rebuilt.

That and the fact that frequent disruptions in the north led to more martially adapt northerners migrating to the south and joining southern armies(the famous Beifu army was largely constituted from these refugees and their descendants).It helped that a lot of Chinese to the north still saw the Jin Dynasty as the legitimate government(this sense of legitimacy stopped after the Song usurpation of the Jin throne and the parallel development of the Northern Wei as a functioning state).The various southern empires never really stopped relying upon northern defectors or refugees as generals and soldiers until after Hou Jing’s rebellion.
 
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