In this case, you do not own, or even control, the software you wrote or the device it's running on, and you must re-install it weekly. In my opinion, sideloading should completely bypass thr manufacturer. I do not need to email Linus to ask if I may run software on my Linux Mobile device, or Cook to run software on a Mac.
To call Apple's allowances sideloading feels disingenuous to me, because of how many asterisks there are attached to it. And I'm not even touching on the requirement that one support Apple's hardware business, either by directly buying from Apple, or keeping second-hand devices valuable and in-demand due to the development environment running exclusively on MacOS.