It might not be the most logical thing to do, but it's not like it's necessarily an immoral thing to do (as "Let's rephrase your statement: 'Paying back on things you've already purchased...'" implies).
It's one thing if the money is borrowed from a friend or family member (as a charity or with extremely below market interest rates). But the 2.43 trillion dollars of debt that you cite is almost entirely with institutions which make a profit off of debt. [not bashing creditors]
It probably isn't even illogical. He makes money in a way that heavily depends on him--his morale and how much work he is willing to put in. I would not be surprised if going on a vacation actually motivated him enough to be a good deal from even a purely fiscal perspective.
Oh yeah, I can totally see that being the case as well. I almost shared a story in my last comment about a guy I knew who, though constantly struggling to stay afloat (most likely below poverty with a wife and three kids), would do his best to buy something nice for his wife (something small, but thoughtful) and sometimes rent a movie that they could all watch when he got home from work.
My dad pointed out "Your family's wellbeing includes their morale."
Either way, only Ryan (and possibly his accountant [probably his wife]) can make that call.
It's one thing if the money is borrowed from a friend or family member (as a charity or with extremely below market interest rates). But the 2.43 trillion dollars of debt that you cite is almost entirely with institutions which make a profit off of debt. [not bashing creditors]