it's not so much how deep it's going, (unless the belt is riding on the shaft/bushing and wrapping around from below) it's the hill you're attempting and the power output of the engine ... the hill is winning the battle.
the tav is going to its lowest range and the engine still can't pull the hill and stalls, leaving the belt locked down in the pulley. you're attempting to restart the engine with it basically stuck in drive.
only recourse may be to re-gear with a smaller sprocket on the jackshaft or a larger one on the axle. if you have a 6" diameter driven pulley, you could go up to a 7 inch one.
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