Before I was on the River Rats, they did break the fiberglass in the transom well on their twin, but caught it before it was a catastrophic failure. They ended up making a large bracket that bolted to the gunnels and made a cover plate for the cracked fiberglass. The transom well was eventually repaired when we had the hull rebuilt, and now there is sweet aluminum plate about 10" x 4" on the top and bottom of the fiberglass where the pylon comes through (it's sweet cuz I made it).
Here is another photo of the same boat from before. Look how far that pylon ripped through the fiberglass. Pretty amazing. I think a lot of teams over estimate the strength of the fiberglass in that area.
The photo submitted was not of their hull, it is of another club's in FL that had the fiberglass rip through. Talking to the driver afterward, he showed that the fiberglass has been reinforced this last winter on the inside with some plates. Pretty beefed up now. I still don't like that way of pulling though. Greg