Just for safe practice, I wouldn't send HUGE amounts at one time. Numerous things could go wrong, ...
Like what?
Like the obvious someone else mentioned. You send it to the wrong address. Sending a 1 BTC test to verify the address is pretty darn wise if you plan to send a total of 100 BTC.
Sending a lot of BTC in one transaction to the wrong address would be a bad mistake, but sending several small amounts to the wrong address would still be the same mistake. I agree that sending a test amount and then waiting for the receiver to verify that they received it before sending the rest would solve that.
But, I still don't see the benefit of sending several small amounts. He wrote that numerous things could go wrong and that was one. What else?