What solid books on the historical and intellectual development of the Talmud would you recommend? e.g.:
The letter of Rav Sherira Gaon - which is the only solid Geonic work we have that traces the development of the Mishnah and the Talmud. There is a lot of historical nuggets that can be gleaned from it.
is a responsum penned in the late 10th century (987 CE) in the Pumbedita Academy by Sherira Gaon, the Chief Rabbi and scholar of Babylonian Jewry, to Rabbi Jacob ben Nissim of Kairouan, in which he methodologically details the development of rabbinic literature, bringing down a chronological list of the Sages of Israel from the time of the compilation of the Mishnah, to the subsequent rabbinic works (Tosefta, Sifra, Sifrei, etc.), spanning the period of the Tannaim, Amoraim, Savoraim, and Geonim under the Babylonian Exilarchs (Resh Galutha), concluding with his own time. Therein, Sherira Gaon outlines the development of the Talmud, how it was used, its hermeneutic principles, and how its lessons are to be applied in daily life whenever one rabbinic source contradicts another rabbinic source. It is considered one of the classics in Jewish historiography.
I suggest Artscroll’s “Introduction to the Talmud” with Rabbi Dr. David Katz translation and footnotes to appreciate it.
I always enjoyed Rabbi Berel Wein's Echoes of Glory which in Section IV explores the formulation of the Mishna and Gemara
Indeed, Rabbi Wein has a bespoke book on the history of the Oral Law entitled The Oral Law Of Sinai - An Illustrated History of the Mishna. The blurb there reads as follows:
Written by historian Rabbi Berel Wein,The Oral Law of Sinai is an extraordinary and beautifully illustrated book that explores the Talmud, a law book that is a faithful transmission of the Oral Law of Sinai. As Rabbi Wein explains, the Talmud is two separate books comprising the Oral Law. This work offers an explanation of the first book of the Talmud, the Mishnah. Rabbi Wein guides the reader through the mysteries of the Mishnah that detail ethical principles and moral values. It is also filled with legends and stories of psychological and historical observations. The Mishnah discusses medicine, pharmacology, dreams, botany, astronomy and mathematics, as well as human and animal biology. There is nothing about human existence, nothing about life, humans, nature, spirituality or physicality that is a taboo subject. All is Torah; all is holiness.The Oral Law of Sinai is replete with humor, irony, pathos, soaring optimism and cold hearted realism, its drama emerges from the give and take of intensive scholarly debate and unending questioning, problem solving, and hypotheses.
You can see a preview on google books here
As far as some of the key personalities of the era, there is a relatively new book entitled The Tannaim & Amoraim: A guide to the Chachmei HaTalmud written by Rabbi Nosson Wiggins. The blurb there reads:
This masterful work brings clarity to the study of Shas by providing concise but enlightening biographical portraits of the main Tannaim and Amoraim, with information and guidance for every level of study. It features:
Historical background -- where and when they lived Biographical data -- who their rebbeim, talmidim, and relatives were Stories from their lives Explanatory notes and source references A helpful index, maps, and glossary Informative appendices for further study An essential guide for the study of Shas!
You can see some sample pages here