What is the lifestyle like for an overnight small air cargo pilot?
It sucks. It really really sucks. Flying in combat felt more relaxing than hauling checks in a frigid old Aztec wondering what was going to breakdown next.
Don't bother checking weather - you're going or they'll find someone who will.
It seems a lifetime ago, but I did the canceled check hauling gig for a couple of years, late '90 to early '93; while it was not an easy job, it was a great experience that I wouldn't trade for anything. Would I do it again? Nah. I was at a pretty decent outfit, U.S. Check, which later became Airnet. We had really good maintenance on the airplanes and virtually no "pilot pushing" from the chief pilot or dispatch. I was Omaha based flying C-310Rs on runs including DSM, STP, MKC, FSD, RST, MDW. It could be pretty boring and routine most nights; summer was hot n sweaty while dodging thunderstorms, while winter was cold, snowy, lotta ice, hoping the boots would work and the heater would keep running. Most nights they did. Some nights would be ILSs to minimums on every leg, 4-7 legs per night. Single pilot, no autopilot, no GPS, all weather... we just went out and did it.
Fatigue was the biggest issue to deal with; my usual run was from 2330 to 0800. Even being on a night schedule,the 0600 launch outta STP to head for home was tough, was really hard to stay awake on that leg. I'd fly 4-5 nights a week, then Sat/Sun would revert back to a day schedule to try and be "normal" for a couple of days. Learning to sleep well during the day took awhile.
Now that hauling canceled checks and overnight film is a relic of the past, there aren't nearly as many old Barons, 402s, Lear 35s flying around all night. I see that GTA runs a few Bonanzas and Barons around, while Central Air out of MKC is still running some old Aero Commanders. Even my old Airnet is down to a handful of Barons and a few Lears. I wonder what they're hauling these days? It's the price of progress I suppose, but it's sort of sad that these jobs have dried up, it was a great way to build time and experience while working toward an airline job.