Weakness of Ashikaga Shogunate

Why was the Ashikaga Shogunate weak? It was unable to prevent the Onin War from destroying Kyoto. At one point it had enough military prowess to force the Southern Court to... well the south and was able to force them to effectively concede to them. Traditionally, Japanese chronicles (those who wrote during the Sengoku period) attributed the inability due to weak character of the shogun at that time, Ashikaga Yoshimasa. Perhaps this is part of it, but I feel like there has to be more than one weak ruler.
 
I thought the issue was the Shogunate was based in the area around Kyoto, whereas most of the good farmland was further north, around modern Tokyo (though of course Tokyo itself was just a village at the time). So the Ashikaga Shoguns just didn't have the resources necessary to keep all their vassals in line.
 
So the Ashikaga Shoguns just didn't have the resources necessary to keep all their vassals in line

if it was simply an issue of not enough money to hire a bigger army, the Kamakura Shogunate (before the Hojos came along anyways) shoudl have been even more precarious.
 
They devolved many powers to the shugo (provincial military governors) which temporarily aided their cause but in the long run brought about the Onin War when Ashikaga Yoshimasa failed to settle internal disputes. This in contrast to the Kamakura Shogunate where the shugo were primarily shogunal aides meant to help organise military and policing efforts (and control local shogunal vassals). Essentially, the Ashikaga Shogunate was transformed into a federation of powerful clans which before long had no need to rely on the Shogunate and were free to squabble amongst each other in the name of settling disputes.

There was also the overuse of tokuso (debt cancellation) to consider which frequently upset the economy. I would also blame economic factors in general, which includes factors like increased agricultural productivity and rise of various ikki groups, decline of the shoen landholding system, etc. These weren't insurmountable, but the Ashikaga were not able to handle this and instead relied on their vassals which would cause the Onin War and Sengoku era.

I blame it on the Ashikaga lacking a coherent vision for the post-Kamakura order, which contrasts with their nemesis, Emperor Go-Daigo, whose reforms set out a coherent vision that seemed to deal with the challenges that felled the Kamakura Shogunate (even if not without their flaws). The Ashikaga came to power as the heads of a coalition of prominent clans, and when they lost their political authority, everything collapsed until resurrected at the end of the 16th century by a new order also capable of dealing with the reality of the time.
I thought the issue was the Shogunate was based in the area around Kyoto, whereas most of the good farmland was further north, around modern Tokyo (though of course Tokyo itself was just a village at the time). So the Ashikaga Shoguns just didn't have the resources necessary to keep all their vassals in line.
They were perfectly capable of controlling the Kanto region through the position of Kanto kanrei (essentially the reverse of how the Kamakura Shogunate controlled Kyoto with the Rokuhara Tandai), and indeed the Ashikaga came from there to begin with, but the Kanto kanrei post was subject to endless intrigue as the Ashikaga declined, eventually leading to it being defacto controlled by the Uesugi clan.
 
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