I've been using a Dewalt 1/2 and a craftsman 3/8 drive for two years now in my shop, haven't touched an air tool since
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Could be the fuel pressure regulator leaking down. Not too familar with the set up but if it has a vacuum line it could be leaking into the intake causing hard starting.
Mine does the same thing on cold days, warming it up doesn't always help. I sometimes think its the cold clutch. It only does it the first time I pull away.