Nick, I like the idea, and have been working on a training manual myself, with a bunch of help from Erik. It's been on hold for a bit, but coming along, and of a similar vein.
Couple quick thoughts, for whatever they're worth...
You need to somewhere specify how you want things done, and this will dovetail into the Formal Training Program in place that might be part of a person's GL policy, my GL through Stratum requires it. My approach is to have default system for a lot of things. Can we generally have a plan in place that is a Go-To rather than re-inventing the wheel and making sure every one knows what the new plan is? This goes with packing the truck, operating trucks/ machines, rigging, etc.
Have a formal driving policy and a sign-off, and a formal driving test for the employee to take, sign off on, etc, and file it. This is important for liability/ negligence suits in the event of an accident.
A Standards of Practice SOP manual would spell this out.
To use as an example, I think you had a criterion for hooking up a trailer/ chipper...
Hooking up a trailer usually first involves
backing up to it (its own procedure),
connecting hitch and locking with a pin,
attaching chains criss crossed at the appropriate length without being too loose or tight,
connecting wires and checking lights,
checking for chocks, obstructions to driving away (anything that will get run over that shouldn't), visual on tires, etc.
Don't pay a a bit better than average wage to get a bit better than average employees. Wages and associated W/C are important considerations, but so is the employee that can head off a blown engine by being diligent about things that you might have to train them on, like what/ when/ how on fluids . The guy that doesn't damage the truck or worse case scenario crush somebody with the truck, will cost a bit more, but will be worth it.
Retention versus retraining costs and lost efficiency.
One thing that I've always stressed with employees is that if they are not sure, they should ask me, and if they don't know that they can do it safely, don't do it, and let me know.
Its a great time for training (teachable moment), saves on injuries and repairs, and let's them know they should ask for training when they need it. I tell them I don't mind taking the time to train them (providing they have a future with me) a couple of times, as need be, and do mind if I have to train them every time, indefinitely.
Hire someone that wants to learn the trade. If you can not afford to pay as much as you would like, tell them that apprenticeship is part of it. The more the learn and implement, the more they earn, because they produce. Short of the desert, there are trees everywhere, so having a marketable skill set develop by working for a reputable company where the employee is valued, and as such is trained and compensated, is worth something. If you need one well-skilled ground guy and two knuckle walking brush monkeys, do that. Know what you need and develop your job positions as such. You might get one good trainable guy to be your saw and rope man on the ground, with a couple of occasional strong backs to supplement based on your workload.
You gonna take that, FJR?! 
