My strong suspicion is that 19th and 20th philosophy was borne out of the age of legalism and lawyers so you get all these complex interlocking arguments so as to argue an airtight case using very specific words with specific meanings.

This sounds like analytic philosophy, rather than continental philosophy. Besides, there's always been freaks who want to logic their way around everything, with varying degrees of success. Spinoza, one of my favorite philosophers, tried to do philosophy following the format/method of geometric proofs in the 16th century.