One observation is they're just not paying enough. Oddly enough, if you're willing to drop $150K there is no shortage of software developers worldwide. People can dehydrate themselves crying in their beer over there being no truck drivers at $20K/yr, but once they offer more than $30K/yr, people will start to line up. For the last couple generations this has been a dog whistle for immigration or H1B style indentured slavery; "We can't find anyone (for $7.25/hr) so we'll have to import".
Another observation is some of your jobs are extremely temporary, like becoming a cable TV installation technician, once the metropolis is wired up in the mid 80s, 99.999% of them are permanently unemployed. So you're going to have to offer fat stacks of cash to drive a truck until permanently replaced by an automated truck in a couple years or have this years flavor of the month of robot certified system engineer cert holders or whatever, because in five or ten years they'll be permanently unemployable or at absolute best case be unemployed and retraining. You can't expect to pay people a low career level wage for an extremely short term job.
A final observation is for real long term careers you've listed, when business people say there's a skill shortage, they rarely mean a shortage of people with skills, because the skills are often pretty widespread and trivial, but a shortage of business people and HR personnel who can CYA on hiring decisions via authority like diplomas and govt licenses, or an established hierarchy like "top 100 biz/med/legal school lists". None of those skills listed are weird or rare in your average human population; you're not asking for research grade theoretical physicists; every house that has a roll of toilet paper in the toilet paper holder has some human who at least vaguely understood logistics; you only need to hire the top 0.001% of that enormous proven skilled population. Its just if you make a mistake in the hiring process you can't act all blameless because he had a MBA from Harvard so I'm not responsible for hiring the wrong guy, or he had a license from the state bureau claiming he was qualified, or he held journeyman papers. Or in summary, its a management CYA behavior problem not a real workforce skill problem.