I just finished "Tikva Memaamakim", R' Yaakov Medan's book on Megillat Ruth. I have long thought that R' Medan does two things better than any other contemporary Jewish scholar: 1) Notice connections and commonalities between widely different realms: individual history, national history, halacha, machshava, minhag, and so on. 2) Express one's complex emotional and religious orientations in a logical manner, through which one's intuitive decisions can be clearly explained to others. (If that made any sense than perhaps I have the skill too...)
To whet your appetite for the book, here are some examples of the second ability.
1) One who fails to perform the mitzvah of yishuv eretz yisrael is punished by karet. Historically this is shown in the deaths of Lot, Yehudah, and Elimelech's families. Halachically it appears in the korbanot of Bamidbar 15:22-25,30 , which apparently talks about positive mitzvot which incur karet, and which comes after the meraglim story.
2) Miriam's tzaraat was a result of her attempts to disinherit Moshe's kids (due to their non-Israelite mother) and thus transfer future leadership to her and Aharon rather than to Moshe's kids. (In the previous story Moshe declared his inability to lead, so a replacement looked likely.) God likens the punishment to "spitting in her face" because spitting is what we do to people who try to disinherit their brothers - see halitza.
3) Boaz redeems land with a shoe, because walking across land (particularly in the original owner's shoe) is a means of acquiring it. Similarly Moshe at Sinai and all Jews in the Temple couldn't wear shoes, because it's not our land being walked on, it's God's land. And in halitza, the guy's shoe is symbolically taken from him: we want him to be disinherited just like he caused his brother to be.