My selection to not ask again is not remembered when I replace an image.
Thank you for reporting this! The "Remember" switch is not persisted between app restarts. It should work when you set it, until you close the app. If it doesn't this is a bug.
It works within the same session.
IMO it should be persistent, as it's very annoying to click it over and over again and remembering for which images it's OK and for which not. Best would be to ask immediately when adding an image, since then the workflow context is fresh and clear and have it persistent.
Persisting it would be easy, but we will also have to build a UI for people to cancel this preference, and make sure that it's discoverable. The most logical place to add this would be the Design Settings dialog. But this means that the setting needs to be set for each design individually. In your opinion, would this be better than the current situation?
Yes, and putting a "store image replacement selection" setting into "Design Setting" (BTW: I would name this project setting, as design settings imply some visual etc. stuff) make sense.
I'm picturing a more robust Settings window in the future lol. Seriously though, it may be worth setting things up like this in the main settings of the app so all the settings for the main parts of the app are in one place rather than all over the place. I don't know about you, but I love it when I can get to all the settings for an app in one window. Tabs work great to add settings for different sections of the app, lots of apps do that so that you can change the settings for particular parts of an app in the sections that make the most sense for them. Would be a great way and a more productive way for editing our settings without having to have multiple places to find them at. :)