Do not fit it without something between the mount and the transom. The gel coat is already cracking, doing that will make it much worse. I would swap the rubber out for a thicker wood backing plate, use a router or sander to round off the edges to spread the load evenly (not 'hot spots'), and make an equally thick wood backing plate for the inside the same way. If you don't want to spend the cash on teak, Starboard plastic lumber could do the job for less, or a 'lesser' hardwood if you epoxied it up thoroughly.
Countersink the holes on the outside of the transom and use 4200 on the bolts and backing plate on the outside only. Do not put sealant on the inner backing plate, if it leaks from the outside you don't want to trap the moisture.
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