the the first problem lies in the GUESSwork of determining the exact boat length away from the overhead structure.
if, standing at the helm, and you had a mark on the mast as the correct height so that your line of sight passing thru the mark was at the predetermined angle, and assuming the boat was at the predetermined distance, you COULD compute the height of an object crossing your line of site beyond the mark on the mast.
but on the water its very hard to determine distance, especially when there is no reference point other than the bridge itself.... if you where near one of the abutments, you would have only a slightly a better reference point to do your guessing from.... and then the second problem is if the water is choppy, its harder to judge, and IF there is any wind or current pushing you towards the bridge, 2 boat lengths or even 5 boat lengths is MUCH to close if you are unsure if you have the proper clearance....