Obviously he's high maintenance and he's a mess handling his own money.
If you keep hiring him or giving him "help money" he'll never learn. Soon he'll ask you to marry him or adopt him...
I think you already made up your mind.
Do you want to be his sugar daddy or not? If you have so much money and he's so good keep on hiring him, after all he's your kept man or at least he thinks of himself that way.