Is my plan to learn workflow automation for three months, then join Maker School and reinvest profits into lead generation realistic?

No, I don't think so at all. You're making a plan that's too far out; who's to say any of this will matter in four months? You shouldn't budget three months of learning automations. Instead, learn automations in the next week and start talking to customers on August 9th. That's the only thing that matters. Don't plan things out in a rapidly changing world—your plan likely won't be feasible in three or four months. You don't know what you don't know, and most of what you need to learn is still unknown. Scrap the lengthy plan and spend a week learning my automation content, go through a tutorial, then sign up on Upwork, send cold emails, record cold DMs via Loom, and start interacting with the market—real feedback beats tons of planning.