It seems nearly everyone goes through a “How hard can it be?” phase where self-hosting seems like it will be a trivial way to save a lot of money. Then you get to learn about all of the things that can, and will, go wrong over time. Great learning experience.
And then there are the rose-colored glasses people who seem to forget all of the troubles they go through with self-hosting. A few companies back we had a guy who insisted on self-hosting some things on premises to save on SaaS costs. The amount of time we spent waiting for him to figure out why the server was misbehaving each week easily cost several times more than any hypothetical savings. Yet when you ask him, he’d claim it was virtually hassle-free. Management liked it because it “saved a lot of money”… as long as you ignore the cost of the time we lost to dealing with it.