For some dumb reason I used to think that hobos were mystical and wise and believe everything they said...now I take everything I hear from a person broker than me with a grain of salt
Interesting! I could see how you thought that. Just because they're homeless and have fallen on hard times doesn't mean they're dumb. But yeah, there's a good chance they did something wrong to be in that predicament, so their judgment could be questionable. 
I never said they were dumb.  I just don't trust them
You're right, sorry for putting words in your mouth. And yeah, I don't know how to engage with them either. As a college student, there are plenty that kind of stalk the campus and ask for spare change. But I have little spending money, so I always have to turn them down