[nuclearnerd]

I am not your team engineer (ianyte), but:

You could get that to work I think sure - it would be a lot like those mechanical suction cups you use to mount go-pros and GPS. The major challenge will be making sure you get a good initial seal with the suction cups. If any air leaks in as you draw the cylinder back, you'll lose any vacuum you created, and you'll reach the end of the stroke without any grip on the tote. This will be double challenging given the totes have textured, corrugated sides. Maybe if you had some mechanical way to press the seals tight before drawing the vacuum.

Also, as bvisness points out, there are easier ways to lift the sides of a (right side up) tote.