I'm really curious to learn more about this period of civil war and what lead to it, socially and politically, but I've been having a tough time finding English resources. The only book I've been able to get my hands on is Samson's A History of Japan 1334-1615. The only problem is it feels like he requires something of familiarity with the subject, as even his account of Go Daigo crams a lot of information into such little space it's easy to get lost.
Are there any equivalents to Adrian Goldsworthy's books on Roman history or Anthony Everitt's Rise of Rome, that combine social and political history as well as explaining military history in a way a complete military idiot can understand?
Thank you so much for your time!
I'm not familiar with the sources you cited, and I am not especially good with military history, but this is more or less my field so I'll try to answer.
Samson is really old (1960s, by memory) and probably not the most reliable source anymore, so I would steer clear. For Hideyoshi, you really can't go better than his biography by Mary Elizabeth Berry; it has some chapters on Sekigahara as well. Jeroen Lamers wrote the book on Nobunaga, the slightly earlier warlord, that you may find interesting as well. While not directly about Hideyoshi, Charles Boxer's The Christian Century offers an interesting perspective and remains very relevant despite its age.
I am not actually aware of any good general of the Sengoku period; I know there are plenty of popular works, including by that Stephen Turnbull guy who churns out books about samurai bushido every other year. Since he deals with military history, you might find him interesting, but he is much disliked by the community because he basically offers historical trivia and continues the samurai myth without any real analysis. I would personally steer clear.