Why did Richard need to ask for a job?
Didn't his father own the company??
"I'd say this cloud is Cumulo Nimbus."
"Didn't he discover America?"
"Penfold, shush."
Operating on total speculation here...
Richard was a known troublemaker well before Frank was involved in his life; it's possible that Richard's parents wouldn't support him financially after x number of screw-ups, and/or Frank's murder was the last straw.
Remember the scene in which Matt goes to a bar and tries fishing for info from one of Richard's relatives? I can't remember if it was Richard's brother or cousin, but whoever it was confessed that he never really spends time with Richard, or talks to him. It's possible Richard was severely estranged from his family.
I agree that Richard's family was probably fed up with him. I wonder if the reason they bailed him out of jail had more to do with protecting their family business rather than concern for Richard. It was damage control; they didn't want to lose customers because their son killed someone, so they bailed him out of jail and hired a good lawyer. The cannery appears in the background repeatedly throughout the film, hinting that the Strouts probably had a lot of money and influence.
I also agree that Richard and his parents were estranged and they probably weren't giving him a lot of money to live on. We know from Natalie and Richard's conversation in her kitchen that Richard's father was sending her checks for child support, probably because Richard couldn't afford to do it himself. Natalie asked him if his father took him back on at the cannery and he evaded the question.
I don't think the guy in the bar that Matt questioned was a relative of Richard's but rather an employee at the cannery who sees Richard's brother there a lot. I'm not sure he wanted to help Matt, even though he and Frank had been friends. He might prefer to protect his job at the cannery.