Bill and Bob

I believe that Bill is wealthier because he has his family behind him and he has time to be with them. Bob on the other hand sees his kids only a few times a year. He has a lot of money and friends that like him because of his wealth but the minute this wealth runs out they won't be in his life. Bill might have to work harder for less money but he always gets everything he needs and has a happy family. If I had a choice I would rather be Bill for the fact he has more meaningful friends and a good family.

Poor

There can be many factors in some people being poor. In my personal opinion the biggest reason for poverty is your surroundings and situation. Many times people are unable to make ends meet so they have to work deadend jobs with little possibilities of advancement. These people can't afford college to increase their education and chance of getting a higher end job. Many can't do this option unless they're smart enough to get full paid scholarships or athletic scholarships. This is very far and few between as thousands are competing for the same opportunity.
Many other people in my opinion are poor because they have no work ethic and never learned the meaning of work from anyone or any situation. Many just sit around and hope something great will happen to them and people owe them. This isn't the case as it's your life and you have to do the work to get towards your goals. They just don't happen overnight by luck. These type of people I don't feel bad for in the least because they believe "the man" is against them and wants them to stay down.
On a side note to that it's those people that are lazy that seem to get all the help and take money from hard working people. They work many hours a week to get a decent percentage taken away and given to some lazy person that makes up an excuse to screw the system and gain money the lazy way. We need to stop having so many programs to help people because there are many scam artists out there that get away with scamming this money.