Yeah. I have considered that.

There's overlap between empathy and therapy/psychiatry, but also important differences.

Though working with some kind of therapy might suit my personality, and the way I want to work.

I mostly agree with this.

Right now I live in a small town, and my meatspace friends don't need the particular kind of support I can offer. Outreach/community is one of the reasons, maybe the primary reason I'm considering to do studies (academic, certification or something similar).

Still, the internet seems like a viable way to connect with people.

I like the way you phrased that :)

I should probably make clear that most of my knowledge of AI comes from LW posts, I do not work with it professionally, and that this discussion is on my part motivated by curiosity and desire to learn.

Emotions are a core part of how humans make decisions.

Agreed.

Your assessment is probably more accurate than mine.

My original line was of thinking was that while AIs might use quick-and-imprecise thinking shortcuts triggered by pattern-matching (which is sort of how I see emotions), human emotions are too inconveniently packaged to be much of use in AI design. (While being necessary, they also misfire a lot; coping with emotions is an important skill to learn; in some situations emotions do more harm than good; all in all this doesn't seem like good mind design). So I was wondering if whatever AI uses for its thinking, we would even recognize as emotions.

My assessment now is that even if AI uses different thinking shortcuts than humans do, they might still misfire. For example, I can imagine a pattern activation triggering more patterns, which in turn trigger more and more patterns, resulting in a cascade effect not unlike emotional over-stimulation/breakdown in humans.
So I think it's possible that we might see AI having what we would describe as emotions (perhaps somewhat uncanny emotions, but emotions all the same).

P. S. For the sake of completeness: my mental model also includes biological organisms needing emotions in order to create motivation (rather than just drawing conclusions). (example: fear creating motivation to escape danger).
AI should already have a supergoal so it does not need "motivation". However it would need to see how its current context connects to its supergoal, and create/activate subgoals that apply to the current situation, and here once again thinking shortcuts might be useful, perhaps not too unlike human emotions.

Example: AI sees a fast-moving object that it predicts will intersect its current location, and a thinking shortcut activates a dodging strategy. This is a subgoal to the goal of surviving, which is in turn is a subgoal to the AI's supergoal (whatever that is).

Having a thinking shortcut (this one we might call "reflex" rather "emotion") results in faster thinking. Slow thinking might be inefficient to the point of fatal "Hm... that object seems to be moving mighty fast in my direction... if it hits me it might damage/destroy me. Would that be a good thing? No, I guess not - I need to functional in order to achieve my supergoal. So I should probably dodg.. <CRASH>"

1. Having high self-awareness of his strengths and weaknesses as a salesman

That's not at all the same thing as having high self-awareness overall

1. Understanding people well enough to sell to them

Which may well be not very well at all. Understanding people in the context of sales is not the same as understanding then generally.

1. Accurately perceiving reality (understanding physics, peoples' motivations, how to drive to work, how to not act crazy, etc.).

Which most people do. (though actually an accurate understanding of neither physics nor people's motivations is required to get by). I was taking about the "litany of Tarsky"-esqe desire to always seek the truth, even if unpleasant and emotionally painful to learn - which Harry has and very few people generally do.