⭐ Merited by NeuroticFish (3)
If/when he has campaigns to be managed, especially (but not necessarily) if they're more than one and the payments are not in the same day of the week, he may have to handle bigger/big amounts of money/bitcoin on a weekly basis.
I'd say it's even more important to have a secure system when handling someone else's money.Quote
I don't know though what does a HW show when one makes a transaction with 20-40 outputs... 
See:using a Trezor to sign a transaction with 54 outputs was not fun 
With enough receiving addresses, creating an unsigned transaction online and signing it from an offline PC might be faster than using a hardware wallet.