A washer is essential for this application. Else the nut will dig into the soft wood and provide not enough holding pressure. I would fill the hole with a tight-fit dowel and epoxy and re-drill — but before taking that route wait for comments by more experienced folks here who may tell if that’s a no-no.
As for drilling squarely here are some tips that work well for me:
(i) clamp a narrow straight piece of wood (or a ruler) to the leg so that it points perpendicular to the leg in the horizontal plane. Then use it as a reference for the bit.
(ii) stick an old CD to the face of the leg with reflective side out. Use the reflection of the bit on the CD to keep it level in both horizontal and vertical planes. This works very well as long as the bit is 3/8″ or thinner and that’s plenty for this application. But its hard to operate brace and bit at eye level. Again, easier to do this if using a hand drill.
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