Having been in both positions, my experience is that a whole lot of the idea that cloud is "cheaper" comes from people without awareness on how much of a commod

Having been in both positions, my experience is that a whole lot of the idea that cloud is "cheaper" comes from people without awareness on how much of a commodity the skill set to set up and manage non-cloud setups is. You can reduce this all to predictable monthly bills scalable up and down by small fractions of headcount with ease most places. At the very small scale when trying to start something, do what you're comfortable with, because whatever you're not is likely to cost you time. Above that, it's down to what your margins are like, and how large a part the hosting is, but it's rare for cloud to be the cheaper option. Certainly not at list prices - while you're small enough to pay list prices you're being screwed over massively.