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When connecting two progressive actions, are you supposed to connect them using progressive in both or only the last one, as tense should be determined by the last verb?
Example: He was sitting in the classroom, reading a book.
彼は教室にすわって本を読んでいた。
or
彼は教室にすわっていて本を読んでいた。
Thanks in advance
Both of these would not express progressive actions. When you connect verbs with て-form, it would mean you finished the first action, then did the second action. 座っていて would be ungrammatical because you imply a progressive action is already done. Instead, for progressive actions, you would add ながら to the end of the ます-stem of a verb.
彼は歩きながら携帯をいじっていました。
He was messing with his phone while walking.
For your example, however, this gets a bit more complicated. Sitting in Japanese is an instantaneous action, not a state. While you can say you were "sitting while talking" in English, 座る means the action of sitting down and is instantaneous. You cannot "read a book while performing the action of sitting down". Instead, you would "sit down, and then read a book".
So, instead of:
彼は座りながら本を読んでいた。X This is incorrect
you would say:
彼は座って本を読んでいた。
He sat down and read a book.
V1 + て + V2 can mean "V2 while V1", not only "V1 and then V2". How do you explain 泳いで川を渡る, 歩いて学校に行く, 包丁を使って野菜を切る and so on?