Re: Person A and Person B, I don't think it's a clear cut as that.
As for "people" saying get a job etc, I think whatever anyone does (whether you're a banker or a shopworker or the Duchess of Cambridge ) there will always be judgement and unsolicited advice, the trick is to just ignore it and find better social circles. I do think it's worth getting a job you love and are challenged by for YOURSELF though, not just to get dates?
I am sure we all know "person A" types who have great relationships with attratictive women.
But then they go for women who are similar age/education level/physical attractiveness level? Within their actual peer group? Women who reciprocate their affections?
Most male acquaintances I know who claim not to get a woman because they are "too nice"/women are all golddigging bitches who only want six-packs (or even claim it's down to race or similar) are a bit deluded in terms of what they think they can attract - they claim women are shallow but they themselves only chase after childless size eight younger than them types.
They take some nineteen year old Brazilian waitress (or someone they have nothing in common with intellectually) out to dinner and then "golddigger shame her" if she doesn't want to pursue a serious relationship with them.
And also, dating is a free market? We don't live in Saudi Arabia.
People can go out with who they want. Long term, there'd be advantages and disadvantages to either option.