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Feb 16, 2018
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My parents are Indian citizens and are visiting Toronto on multiple entry- visit Visa . My brother is across the border in Detroit . My parents have US B1 visa too.

Can they shuttle between US and Canada multiple times ( expected to be 2 or 3 times over 4 months period) by road. Will there be an issue ? Have anyone done this before
 
shouldn't be an issue at all as long as they leave the US each time within the amount of time they promise at the port of entry (not the i94).
their entry the second and third time will even become easy since their previous I 94 will still be valid. Just be truthful to the officers, everything will be ok.