When Biff suggests that Happy leave home and head out West with him, Happy initially seems interested but declines the offer. Happy seeks gratification from others and would rather become a success at home, where his bosses and colleagues can witness his accomplishments. He tells Biff,
I gotta show some of those pompous, self-important executives over there that Hap Loman can make the grade. I want to walk into the store the way he walks in. Then I’ll go with you, Biff.
In contrast, Biff refuses to stay home because he cannot stand his father, Willy. Ever since Biff discovered Willy having an affair, he has lost all respect for him. Biff also cannot live up to Willy's expectations, and being under the same roof as him is a constant reminder of his personal failures.
Biff and Happy avoid getting married and settling down for a variety of reasons. Happy is a selfish womanizer; he enjoys living a promiscuous life. He brags to Biff about sleeping with different executives' wives and is a notorious adulterer. He also harbors fantasies of becoming a success in business and does not want married life to interfere with his dreams. Although Biff is thirty-four years old, he is still searching for a steady career while trying to chase the American Dream. Biff's relationship issues stem from his father's marital problems, and he also struggles to be with just one woman, like Happy. Overall, Biff and Happy are too selfish and insecure to meet responsible women, get married, and settle down.
Biff won't settle down because he's still traumatized over finding out that his father was having an affair with a secretary. This also explains why he's not prepared to stay; he's reached the point where he can't stand to be under the same roof as Willy.
Happy won't go out West because he hasn't yet achieved anything in life. Deep down, despite his outward confidence, he's not sure if he'll be a success out West. The last thing he wants is to have to return home to his family with his tail between his legs, not having staked his claim in the world as he and Willy had hoped.
As for not settling down, Happy is too much of a womanizer for that. There's a certain immaturity about his attitude toward women that makes it nigh impossible for him to settle down in a long-term relationship. Happy has internalized Willy's philosophy that all you need to be a success in life is to be a well-liked man. Among other things, this means that, so long as he continues to attract the attention of women, he'll be more than happy to return their interest.
The answers to both questions lie in the complicated relationships between sons and father. Happy, as the younger son, has grown up in Biff's shadow. He feels a deep-seated need to prove himself to his father. Hence, he won't go west until he can achieve his father's approval. Biff can't...
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stay because he has no respect for Willy. Ever since he discovered his father's affair years ago, Biff harbors a hatred and disgust for his father which often erupts in anger. It also leaves him unable to be satisfied in any job or location for very long: thus, his restless wandering.
The second question is a bit more difficult to answer, but falls under the same reasons as the first. While we can't really answer why someone doesn't get married (I mean, it's not like one can walk up to a stranger and marry instantly), we can trace the problems in Biff and Happy's relationships. Happy is a notorious adulterer and womanizer. Biff never mentions a girlfriend, and seems uncomfortable with the idea. Both of these problems trace back to Willy's relationship with Linda. The sons have seen their mother bullied, emotionally abused, and ignored their entire lives. Biff also knows his father has cheated on his mother. So there's definitely unresolved issues in dealing with their parents' relationship. This is the most likely reason that Happy and Biff cannot "settle down".
In the very first Act, when we see the brothers together by themselves and they discuss their lives and what has been happening to them, Biff invites Happy to go West with him. Happy is certainly willing, and definitely feels attracted to the idea. However, note what he says to Biff eventually:
I gotta show some of those pompous, self-important executives over there that Hap Loman can make the grade. I want to walk into the store the way that [they] walk in. Then I'll go with you, Biff. We'll be together yet, I swear.
As the audience watches more of the play, they understand that Happy has swallowed his father's dream that any man can make themselves big in the city if they just have enough drive and commitment. Happy in particular, perhaps because as children Willy clearly favoured Biff, feels a real need to show that he can make a success of himself as Willy would have wanted him to in order to gain his father's approval. It is very tragic that even though Happy would probably be happier out West, his adherence to his father's dream keeps him in the city in a dead end job where he is only able to show his supposed "superiority" to his managers by sleeping with their wives.
In addition to the previous answers, another thing to take into consideration is money. Neither Biff nor Happy have any form of financial stability to even come close to maintaining a home. Add that to their psychological immaturity and the co-dependence they have of each other as brothers. It is very hard for two young men who have been engrained the idea that money buys everything and IS everything. Biff and Willy lack the very thing that their father told them was the formula to be happy. They are as lost looking for the key to happiness as their father was. There is no room for any other goal in life when one is fixated on a specific one.
The previous post was very thorough. Indeed, the boys' own experiences with the notion of "happy marriages" such as their parents' have made it difficult for them to be able to accept that marriages work. There is a certain challenge present for the boys in being able to buy into the concept of marriage when their own narrative with it is replete with emotional distance and adultery within it. The fact that both sons blame their parents, specifically for much that has gone wrong in their own lives indicates that they are not in a moral or psychological place to accept the responsibilities that come along with marriage. Biff blames his own failures on the disillusion caused as a result of his father's indiscretions and becoming aware of them at an early age. In the end, Wily's own failures impacts Happy to make "right" how Wily was seen, but nowhere in this belief does one get the idea that the personal realm was a part of this. It doesn't seem as if Happy is one who is fully able to see that Wily's own failures in the personal realm is one of those areas where rectification is needed, and in this light, the same disregard for the personal is seen as it was with Wily. For these reasons, it doesn't seem like the boys are going to be predisposed to being able to "settle dow" in a conventional sense.
Willy's high expectations for his sons interferes with their abilities to form lasting relationships. Biff sees the reality of Willy's life, and wants to distance himself. Happy is content to live in Willy's delusions. Neither situation is conducive to dating and marriage.
Additionally, neither Biff nor Happy hold down satisfactorily paying jobs. Willy has set them up for failure in business and in love. By living in a fantasy world and pulling his sons into it, only Linda really lives with the daily rational truth.
Both Happy and Biff are lonely and bored, but neither has the capacity to declare independence and follow his own path. It's part of the tragedy of Willy Loman.