Nobody educated thought the Earth was flat. But Christopher Columbus miscalculated the size of the Earth, and everyone else correctly calculated it.
There was no way that Columbus's ships could cover a distance equal to the width of the Atlantic + the width of the Pacific + the width of North America. They would've all starved to death before they reached their actual goal: the islands east of Asia (or Asia proper).
It wasn't a calculated risk to find new land, they were trying to go to existing land and Columbus was just convinced that it was much, much, much closer than it actually was. Despite the fact that pretty close estimates of the size of the world had been calculated for a long time before him.
There's a difference between being wrong and being irrational.
Serious flat-Earth thought was ideologically motivated in the late 19th and early 20th century and bears some interesting parallels to climate change denialism.
Among educated people able to afford and read a copy of Eratosthenes yes, but there were probably a lot of ordinary people that were not literate and were never exposed to any actual evidence to the contrary,who believed it was flat.
Flat earthers in the modern world really do have no excuse, education in the basic geometry and simple tools they need to prove it themselves is near universal in the Western world, but back then it was perhaps more understandable
who were the ones capable of funding the project in the first place
uhh.. no it wasn't?