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What would be the best paying career path for someone who is hard working but not born very bright when it comes to dealing with people (and is willing to work his/her best to overcome this natural weakness)? Assume this person has no family connections to speak of either.
It depends on what they like and what they're good at. I can think of many jobs that pay well yet don't require social skills. Plumber, electrician, garbage collector (my personal heros as I really wouldn't want to live with my own refuse ), snow plow driver, landscape, construction, lab work, computer programming, CAD,...etc, etc, etc...
The fact of the matter is, most jobs don't require social skills. Trust me, I was an engineer and worked with lots of engineers who were lacking in social skills. Unless you're working with the public, it's not an issue and if you are, you get used to it.
It depends on what they like and what they're good at. I can think of many jobs that pay well yet don't require social skills. Plumber, electrician, garbage collector (my personal heros as I really wouldn't want to live with my own refuse ), snow plow driver, landscape, construction, lab work, computer programming, CAD,...etc, etc, etc...
The fact of the matter is, most jobs don't require social skills. Trust me, I was an engineer and worked with lots of engineers who were lacking in social skills. Unless you're working with the public, it's not an issue and if you are, you get used to it.
Whoa, as an engineer, you never had to work with a team?
I have rarely seen a job that doesn't require some social skills. You have to get along with those you are working with *and* with your manager, etc.
It is true that some jobs require less of this especially if you are not working with the public. Working some jobs on the graveyard shift will get you left alone as well.
Off-hand I can think of several good fields - computer programming, reference librarian, copy editor, mechanic, small appliance repairman - but even in these jobs some contact with others is required and you might have to sell yourself to your customers.
Flight attendent, believe it or not...you don't deal with the same people, only people for a short flight, while you are busy serving drinks, you don't even generally talk to your crew mates, you are so busy working, if you have the front section, you work alone, for your 10 rows of people, giving out drinks, picking up cups. You only deal with a crew for one month, then you get a whole different crew the next month. If you work on call, you never work with the same people at all...so even if you have horrible people skills, as long as you are nice, show up to work on time, and do your job...no problems...you don't have to maintain long relationships with anyone.
But if you really have social problems, work night crew at a prison, you don't have to talk to anyone at all. Or another good job, is to be a snow cat operator, you work at night, in your own snow cat, grooming runs for ski areas, you never talk to anyone, your boss just hands you a schedule...
I think you are focusing on the wrong thing. Instead of starting with what you aren't good at, consider your talents. Then, you can narrow down from there.
So....do you enjoy math, science, computers, language....
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), snow plow driver, landscape, construction, lab work, computer programming, CAD,...etc, etc, etc... 
