Newbie question: Is the job site you walk into ever plumb, square, and level???

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I've recently changed careers to something that's turned into a lot of residential construction (long story there), doing bits and pieces of almost every trade. Anyway, my construction mentor and business partner knows what he's doing, but ALLLWAYS far underestimates the time any particular job will take, almost comically so that it's a sad running joke between us, because what looks simple, like finishing a sunroom, turns into a job 3x as long because every window was framed slightly differe...