1) I do not know which college is easier to get into or is more affordable but I would think that it's a bigger hurdle getting a student visa after having found the college. He will have to prove strong ties to his home country so they will believe he is going back when his visa expires.
2) He can work on the campus of his college, internal jobs, without a work permit. If he wants to work outside of the campus, he needs to wait until he has been studying for 6 months, then he can apply for an off campus permit. This permit would allow him to work up to 20 hours a week during weeks of school and full time during holidays.