Memphis, are you sure you want to use Waco Jacko and Crazy Mike as an example to prove your point? These morons had no financial planning, had very serious legal troubles and were so distant from realty that even Disneyland looked more real than their fantasy land.
As Clubshaker mentioned, it is really not that expensive to have cleaning service come in and not only clean your house but also take care of most other chores on biweekly basis. They charge less than what most people would perceive. Also, there are plenty of landscaping services that will take care of the outside of the house. In some subdivisions, it is included in your HOA fees.
Wining a lottery means that you would have enough resources to not only buy what you want at the moment but also secure your future income. There are plenty of money managers that do this for a living.
My point is very simple; if someone has the money to buy a multimillion dollar home, no matter where the money came from, they will also have enough resources to maintain it.
The “Dream House” in the title of this thread does not mean that a certain property can be owned only in dreams; that is how realtors describe most upscale homes here. Go checkout any large realtor website and see how they describe the homes to entice the buyers.