The Last Harbor Pilot. The Harbor Pilot Series, #1

Milo Vantage has boarded six hundred and thirteen ships that weren't his, flown them through a debris field that rearranges itself every eleven hours, and handed every single one back without a scratch. His reward: decent pay, terrible coffee, and a business partner who has been cataloguing his personality flaws, alphabetically, for eleven years. He also owns the largest private collection of old Earth memorabilia in the Corvid Reach - including a cassette tape he can't play, a trading card of a man in heroic shoulder pads, and strong opinions about a civilization that smoked cigarettes in maternity wards and still somehow reached the moon.
Then a captain with an ex-military handshake and a cargo manifest full of lies hires him for one simple run. The cargo isn't medical supplies. The colony at the far end is out of second chances. And back home, a very reasonable man in a very expensive suit is about to prove - live, on every screen in the sector - that pilots like Milo can be replaced by an algorithm. The algorithm has processed three years of flight data.
Milo has instinct, spite, a four-armed rigger who never doubts the paperclip, and the collected wisdom of a century that solved most of its problems with a training montage. It should be simple enough. With him, it rarely is.