Comment by ecairns

This seems very insightful to me. I think I'm another data point that mostly fits your observations.

Individual psychology definitely plays a huge role with me personally being on the far side of guess culture. I have pretty extreme social anxiety and the idea of asking someone for something fills me with dread every single time. Not because it shows weakness (I think), but because I don't want to impose on others. Asking someone I don't know for something is almost impossible. I can barely do it in a context where it's expected, like customer service.

I'm not wealthy, but I have moved around a bunch, especially as a child. I'd absolutely help out anyone who asked for it, but also try anticipate the needs of others.