The Daily Life of a Great Director

Akina Nakamori, Rie Miyazawa, Hitomi Kuroki, Miho Nakayama... A film studies doctor transmigrates to 1990s Japan, where the economy has collapsed and beautiful women are everywhere. He vows to become a renowned director.

PS:

A note on terminology: In Japan, a kantoku is a chief director with much more authority than an ordinary director.

The protagonist is cautious and scheming. If that's not your thing, don't read.