Rich people mostly hang out with rich people, so preference notwithstanding it’s expected they’d find partners from that pool. As for preferences, I’d guess it varies a lot person to person but averages out to a preference for people with at least some status.
In the US, debts of the deceased are paid out of the estate. If there isn’t enough money in the estate, the debts just go unpaid—descendants or other survivors are not responsible.
In your scenario, assuming he owned the residence, it would be sold and the debts repaid from the proceeds; likewise with any other assets he left behind.
Love is what separates a crack house from a crack home