I can imagine an AI agent grappling with all that but the first time a Dash button price gouged me that way I'd throw the thing straight into the trash.
There is still the issue of who is paying for said item and building an open platform that allows another individual to use my funds at the press of a button would require a lot of investment (identity, trust, limits, etc) though I do see the value you are proposing showing a "mini market" to select from.
I never got one, but they certainly made sense in my mind for something like laundry detergent, etc. You notice you are getting low, hit the button, forget about it and 3 days later it shows up and you go "oh, right perfect".
Envisioning the gigolo opening up their nightstand drawer, shocked they're down to their last couple rubbers... slapping the button and getting back to some other slapping.
I really liked the dash buttons for two reasons:
1. It made ordering something you regularly and only buy online anyway easy for an entire household, like for my use case, hookah coals roughly every month.
2. You could place the button next to where you store said consumable and most folks would prefer using it over asking for a link or reminding someone else to re-order.
I do think it was a mistake to launch with an initial limited set of branded buttons for common household goods most people pickup at the store anyway (like detergent) instead of a generic button for my point 1's usecase but thats just plain-old BigTech thinking.