Overall fun (and funny!) in concept, but I think the basic gameplay was a bit too tedious (which I guess was kind of the point). It got a good chuckle out of me anyways!
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Always remember, it's a feature, not a bug! ;P
I think an idea to make it more fun could be to be able to choose which part to automate each day, until it is actually completely autonomous (fake it till you make it!). Like, an upgrade could be to highlight all items on the right stack with a lower value than the currently left one selected. Another could be to further filter by only highlighting those of the same company as the one currently selected. Another could be the ability to sort by price and so forth. That would add a winning condition as well.