The idle rich have both money and time on their hands. Paying someone to do work they could easily learn to do themselves gives them even more time. It also gives them the psychological satisfaction of pushing around people who are far beneath them on the socioeconomic scale and bragging about it to their peers. I have met people like this in San Francisco and I do not ever want to be like them. The behavior is self-reinforcing and enhances class solidarity among the only social class that matters. It also carries moral peril. Devaluing human life is easy when the handiest measuring tool available is a checkbook.
Most outsourcing decisions are thankfully practical and born of necessity rather than luxury. Spending for expertise or other outside help makes sense if it obtains an otherwise remote level of quality. Opportunity costs are useful here. The cost of acquiring a skill or asset on one's own may be greater than the cost of hiring a ready-made capability.
I host my website with a cloud provider. It is far cheaper than buying my own server, learning to be a sysadmin and DBA, and running a dedicated 24/7 high-speed connection just so the Alfidi Capital website is available all the time. I spent a smaller amount of money because the cloud's scale delivers a very efficient solution. We make the same decisions when we buy groceries instead of raising our own crops. Trading dollars for hours is easy when the benefit is immediately clear.
The choice is less difficult after calculating the DIY cost. If I absolutely cannot easily do something myself, and the cost of learning a new skill takes too much time away from my real money-making activities, then paying for an outside solution is acceptable to me. The choice is even easier if I don't have to directly engage a human being. I prefer that others do whatever they are meant to do in their lives. Their time should matter as much as mine.