Put me in the "don't bother to dig that deep" team. i wouldn't bother to dig that deep : the soil that deep will be low quality soil, it will be too cold for the tomato to be in...
If you really want to maximize the roots, try 'regular' deep planting and if that wasn't enough try to make a horizontal trench and plant the tomato somewhat horizontal in stead of 90° vertical, as much stem as you put in the ground that will be full of roots.
You would have a hard time in my ground when it's warm to drill with your macGyver drill, and all you dig up will be crappy compacted 'dead' soil you want to get rid of (so not mixed with the good top soil).
But if this works better for you than that's your way to go.
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