Yes - Making the holes oversized and filling them with epoxy and then redrilling is the correct method. So are the backing plates. I strongly suggest drilling the final bracket holes, one at a time, and inserting a bolt in the first hole before before drilling the second and so on. We found it difficult to hold the bracket in position due to its weight while marking the holes.
On my boat, we discovered that some of the old transom core was rotten while we were drilling the holes. So in additon to oversized holes and epoxy, we drilled rows of 3/8" holes into the transom about 2" apart from the inside, up to, but not through the exterior skin. Then we inserted short pieces 3/8" hardwood dowel , dipped in epoxy (you only have to dip the nose of the dowel, enough epoxy will scrape off while you're inserting to cement to the interior skin) and gently tapped it home. After curing for a day or so, we cut off the interior excess with a sharp chisel and a hammer. Result was a very stiff and, hopefuly strong transom, we think. Anyway we are showing no flex at all.
On my boat, we discovered that some of the old transom core was rotten while we were drilling the holes. So in additon to oversized holes and epoxy, we drilled rows of 3/8" holes into the transom about 2" apart from the inside, up to, but not through the exterior skin. Then we inserted short pieces 3/8" hardwood dowel , dipped in epoxy (you only have to dip the nose of the dowel, enough epoxy will scrape off while you're inserting to cement to the interior skin) and gently tapped it home. After curing for a day or so, we cut off the interior excess with a sharp chisel and a hammer. Result was a very stiff and, hopefuly strong transom, we think. Anyway we are showing no flex at all.