Do you find it easier to trust people who don't seem to care about their own social status?

What should you avoid doing when asking someone for money to keep from damaging the relationship?
Can a doctor ever understand a patient as well as someone who has lived through the same struggle?
What kind of people choose to live in hotels year-round, and what keeps them from moving into traditional homes?
What are some examples of successful people who are perceived as uneducated or unintelligent despite their formal education?