Yes, I think it really depends on what the software does and what I'm using it for (my willingness to invest time). If it's something I use every day for years

Yes, I think it really depends on what the software does and what I'm using it for (my willingness to invest time). If it's something I use every day for years on end to make a living, then I probably want to be able to tweak and customize it (and I won't mind doing it). Just don't make me keep doing it because your evergreen software keeps updating and changing how things work. If it's something I "barely" use, then I have absolutely no interest in customizing it. It should just work. For example, if all I want to do is securely share a file with someone, then don't make me jump through hoops to use it. If however I was looking for software that let me share organized groups of files, should sort in a specific way, would expire after a certain amount of time, and to track engagement with these files (downloads / views), then are probably a few settings I will want to tweak. What I think often happens is software will evolve / pivot to do more (maybe sometimes less?) then it was originally designed to do. Unfortunately that evolution some times lacks a different design perspective. You might have been religious about clean and simple in the original product, but now it's a bit more nuanced, and you'll need to be more flexible. I don't think there's an easy solution. We just need to recognize that as features are added, design still needs to be part of that process.