Why not use grippers to pull them? Probably more effective because there's no root to grow back from, shouldn't require too much force when they're small/the soil is damp, and you don't have to figure out torsion/"friendly fire" from a spinning blade.
I think the project difficulty grows at least 10x with all the dust, insects wind, pollen in the air and whatnot even assuming you hide it for bad weather and you have secured very stable mount points. It sure would be cool though.
Roundup is gross anywhere even in small amounts. If water and energy can be provided similarly to stringman, a heating element to deliver a small payload of boiling water usually suffices.