Try solving it with a javascript widget that triggers a click to show the sidebar based on the user setting. This could be loaded based on the attribute value in the view.
The default sidebar setting is a boolean, it's either true or false. You cannot set the setting to both in the same page, they're mutually exclusive, no matter how much conditional formatting you apply. As such, your dual sidebar toggle plan is not going to work.
The only way I can imagine this working is using two distinct layouts, but that would also require you to duplicate every single page (with snippets, I suppose); one copy for each layout.