Many more questions are answered by Bheeshma. Mahabharata 188

'If one loses his wealth, parents, his wife and children, how should one bear such a loss with wisdom?'
Bheeshma's quotes a brahmin; depending on your day it will sound profound or just platitude. Parting is inevitable, no one escapes it. Nothing is permanent and so on. He ends with 'You should give up desires, but it is not easy for the dull minded, does not go away even with old age! Once you have desires it will stay with you till the end like a disease!'

As time passes and all are pulled towards death, what is the best way to behave?
Quotes an intelligent man. 'Do not postpone, do good before death takes you away! Death does not wait for you to finish your tasks. It is better to follow dharma from an young age. It is not easy as you go older. The love for your wife and children will force you to do things which should not be done.'

How do the rich and the poor experience happiness and sadness. What are their characteristics? 
He quotes a brahmin Shyamaka 'There is no happiness or release, unless you forsake. You cannot even sleep without giving. One who sacrifices everything is the happiest.'
 'A rich man has constant fear of loosing his wealth. Money makes him greedy and arrogant, he looses his mind easily, his attitudes change, he always looks angry, is tight lipped and harsh in speaking. He is egoistic, gets carried away easily, thinks he is the most handsome, well-born, a great achiever and rich. He even thinks that he is a superior human being. If he loses all his wealth by indulgence, he will try to steal it from others and will be punished! In one way having nothing is better than all the wealth of a kingdom. You must reason well and understand the real nature of happiness or of being sad. You should not overreact when you are happy and not become despondent when unhappy'.

In spite of  the best efforts there is no money, but desires are never ending, what should one do to be happy?
'By being impartial, not grieving, by truth, renunciation and non-excitement. You cannot be happy unless you are lucky. It is dependent on divine will. Hence to be happy  you should be indifferent to worldly objects and life. There is no one who has fulfilled all his desires, but as long as a man is alive, the needs and desires keep growing. If you yield to desires you are unhappy, the more you renounce desires, the happier you are.