It would seem that a shorter bolt would have less tendency to get bent by the forces and leverage involved. Spreading out the load to the hull with an oak board is a good idea, but
backing plates -inside and out - will also need to be a part of the equation, to avoid the bolts simply pulling through the
wood. Angling the crutches or legs
outboard would seem to make the problem of leverage on the bolts much worse. When grounding out, the
boat is theoretically supposed to be supported by the
keel structure, with the legs simply keeping the
boat from tipping over. It the legs are splayed out, any force on them will tend to twist the fulcrum (the bolt) with the full length of the leg acting as a lever with the weight of the boat on it. Not a pleasant scenario. Hasn’t this been covered in the write-ups and
forums you researched? What kind of boat are you planning to do this with? The fact that you need legs indicates that it’s not a flat-bottomed boat that would ground out fine without them. What is the
draft? Where are you sailing? Unless you can pretty much guarantee near calm conditions for both grounding out and UN-grounding out, the process is not likely to leave your keel- and the keel-hull joint - undamaged.