I am mostly interested in how much freedom they had in starting their own households, as well as acquiring and managing small (clothing, books, personal items) and medium (horses, automobiles) amounts of money, while living with their family.
This is a little outside your period, but you might want to read up on the phenomenon of the Grand Tour. While ostensibly being about broadening young gentlemen's cultural awareness and knowledge of the Liberal Arts, this tradition was often upper class young men's first experience of independence.
That said, when you went on the Grand Tour, there was a specific itinerary, and a specific way to do the tour, specific goals, experiences, ways of understanding art, attitudes towards the locals, tastes to be acquired, etc. (down to even specific people you were supposed to pay a visit to in a particular city.) You were independent in the sense of being on your own away from your immediate family, but you were not really independent in the sense that young people today are independent, in that you have a wide range of choices and ways of experiencing the world around you.