Oh to be clear I meant this would be a per item option you could toggle, to make it ‘stick/regenerate’ like that. It would be a little annoying if you want to set up a whole list of them, but ultimately allow for the basic use cases… I think? Still haven’t fully digested this all myself and kind of airing thoughts as they come 
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That stick regenerate sounds perfect. Not only would it help in this situation but it could help keep some order by sticking or pinning non negotiable items at the top of a list.