He thought it was ridiculous that the young pioneer sister (Who was interested in him) kept turning him down for silly reasons
I don't know where this took place but flying to New York or to San Diego seems like a big commitment. If she didn't have much money she would be completely at his mercy financially and maybe she didn't like that. Also, if she was attracted to him perhaps she didn't trust herself besides not trusting him. I don't think being in that circumstance and turning it down was a "silly reason" at all. I don't know her age but there might have been a difference in maturity besides the difference in education and experience in life.
Most of the other points he makes is valid but her turning him down is something that, from what you told, seems perfectly reasonable for an attractive young lady to do even if she didn't explain it in an articulate way for him to see her point of view.
edit -- now that you explained more about her after I wrote my post I will make no more comment about it since you know her very well