re: How much can I expect to pay to repaint my truck?

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He's not going to get that much sanded, primed, and painted for $350. There's a lot of hours in a job like that including sanding down the peeling clear coat, priming it, then wet sanding it just to get to the paint stage.

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It can be done.

The cheaper shops use lower line paint (Omni, Limco, Shopline, Nason), so they're less than $100 in liquid ($30 for primer, $30 for QT. of paint, $40 for QT of clear). They also employ cheap labor to do the sanding, taping, etc. for $10-12 per hour. The shop would still make $200+ on a 4-5 hour job. We're not talking high quality work or running the job through insurance.