Reddit mentions of Introduction to the Talmud and Midrash

For a good intro from the very basics in video format check this out

The guy that runs the channel has a website where you can get more info and study materials if you want as well. He is more on the reformed side and not conversion focused, rather education focused so it's a good starting place.

In book form there are these two which are excellent starting points:

Introduction to the Talmud and Midrash

Everyman's Talmud: The Major Teachings of the Rabbinic Sages

However as you go through this journey you will run into a lot of Judaic concepts, words and meanings. The best place to get the core canonized understandings of these IMO is Chabad’s Q&A section.
One thing to keep in mind when accessing info from Chabad is that they are very conversion focused and very conservative. Telling someone to learn about Judaism from Chabad is like telling someone to go talk to the Vatican to learn about Christianity, keep that in mind.

Once you get comfortable with the basics and core concepts I wholeheartedly encourage you to explore other expressions of Judaism as in addition to Hasidics (Chabad, etc…), there are conservatives (think Ben Shapiro) and reformed Judaism with there own interpretations. Then there is messianic Vs. non messianic schools so enough rabbit holes for a few lifetimes 😊

Pick up:

Schiffman's From Text to Tradition, a History of Judaism in Second Temple and Rabbinic Times: A History of Second Temple and Rabbinic Judaism
Ben Sasson's A History of the Jewish People (parts 3 & 4)
The Cambridge Companion to the Talmud and Rabbinic Literature
Lee Levine's The Rabbinic Class of Roman Palestine in Late Antiquity
Hershel Shanks' Christianity and Rabbinic Judaism: A Parallel History of Their Origins and Early Development
Jeffrey Rubenstein The Culture of the Babylonian Talmud
Safrai, Shmuel, ed. The Literature of the Sages. Vol. 1 and 2. Assen- Van Gorcum; Philadelphia- Fortress Press, 1987-2006.
Stemberger, Günter and Hermann Strack. Introduction to the Talmud and Midrash.
Avi-Yonah, Michael. The Jews of Palestine- a Political History from the Bar Kokhba War to the Arab Conquest.
Neusner's A History of the Jews in Babylonia (several parts)