This is exactly how Syntax 1 was taught at UC Santa Cruz when I attended.
We started with a general question of "What is the simplest sentence you can think of?", and then moved to "How could you represent that symbolically? Generically?". With the professor's guidance, the solutions and systems of representation evolved over the course of the quarter to become more rich and complex, and just so happened to trace the development of syntactic theory from roughly the 50s to the 70s. Then you took Syntax 2 tracing roughly the 70s to the 90s, and by the end of that time, you were ready to look at modern problems.
We started with a general question of "What is the simplest sentence you can think of?", and then moved to "How could you represent that symbolically? Generically?". With the professor's guidance, the solutions and systems of representation evolved over the course of the quarter to become more rich and complex, and just so happened to trace the development of syntactic theory from roughly the 50s to the 70s. Then you took Syntax 2 tracing roughly the 70s to the 90s, and by the end of that time, you were ready to look at modern problems.