So another data point. I met a cashier at Walmart who had her last day at work and was moving across country, she was excited, chatty and was willing to load my BB.
Long story short, 5 loads $500x5 on a single BB, all from 1 register. I really wanted to know if there is a $1999.99 limit per register -- it appears there isn't one.
Before anyone jumps on me to "stay under radar" and all of that, this cashier offered to load as many times as I wanted, there was no one behind me and I never load (or plan to) more than 2x$500 with a human at a time. But this experiment worked, and it was on 10/23.
Cheers,
PedroNY