I’d be curious to hear opinions on how much he should have asked for—what could he have gotten away with and still landed the job? Would $1,000 (in 1982 money) have been too much?
I think he picked a good number. It clearly wasn't $1000 of effort. Jim may not have been interested in hiring someone who, like his previous software guy, was looking to shake him down for as much as possible.
$100 in 1982 is about $275 today. $1k ($2.75k today) feels high to me because of the combination of unknown teenager and the fact that programmer pay was relatively lower in 1982. And if you scale that up to $4k per week that’s $11k per week in today’s money which feels pretty crazy for a teenager. $400 per week in 1982 is a salary of like $60k in today’s money. At 20 hours per week that sounds like a good deal.
In the late 1980s I did computer work for a small business and was paid about $9/hr. It wasn't really programming though, more of an operator job with some hardware maintenance/troubleshooting mixed in as needed. My first job as a programmer, in the early 1990s, paid $32k base plus overtime and a yearly bonus.