Job found.

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Same boat as a bunch of other people, unfortunately. My company (big 3) isn't pulling in many more this year, and has stated they are evaluating next year. Nobody can get enough planes. If he doesn't have his first class medical, go ahead and spring for that.

Tradewinds says they are hiring. I know nothing about them.

https://www.flytradewind.com/pilots/?fbclid=IwY2xjawJ13QxleHRuA2FlbQIxMABicmlkETFXcU1sY0NhZHQ5V1ltQVVoAR4_uraUOnY8tsvKC9nqHsz3rYdT5Nnpave944iDKR7JKQ1o0x7XTqBnARNwUg_aem_0aJiJe-E2gjg_xvVU4zvSA

Tell him to go in person to drop zones for skydiving and ask around. Pipeline work. CFI/CFII/MEI - costs money but builds time once you instruct, and can be done around other work.

Is he in a position to buy a cheap 150, and time build?

Search Time Building [STATE] groups on Facebook. Not free, but cheaper than paying outright.

Military - not ideal due to contract (10 years) but Guard/Reserve will pay for flight school, and he can work a second job after that.

I would not accept no pay jobs. Multi Engine time is ok in piston, it's turbine/turbo prop that will bode better for him. Check out pilatus jobs.