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Can a basement dweller that knows everything about DOS get a decent job?

I am a basement dweller with no real skills whatsoever. I do have a High School Diploma, but nothing beyond that. I have below average social skills as well.

However, I know just about everything there is to know about DOS and Windows 3.x. Can I get a decent paying job with that?
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DOS is long dead, so is 3.x, but those skills are used in lots of other things as they are the base for most.
Can you afford to upgrade yourself to focus on modern skills?
Pick something you like to do and specialize in it. Also look on sites like Indeed or Linkedin to see what jobs are popular right now. See what programs your local College offers. If you can get a bachelors degree that would be ideal.

Personally I really enjoyed working with Mirth and Cloverleaf, those were fun. I hate anything Web related, but lots of people are into that and it is always a destination if you don't mind it. Epic has a lot of programs that need skilled people. Check into that.