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Hey jus - welcome to SN dude. I have a C27 myself (OB version too). I have a couple of cracks in my transom from where the OP had mounted the outboard on a bracket without proper backing (instead of using the outboard well). It created a couple of cracks and delams around the outboard well opening and the bracket bolt-holes. Structurally, it's not that big of a deal as there are no direct loads there.
However, your cracks look a lot nastier since they are right where the name plate is. That nameplate could fall off at any moment causing grievous bodily harm and huge embarrassment in front of the ladies. Next time you might want to back off the torque on those screws.
Seriously, you should get that fixed. With the outboard well opening through the transom, that's your main support "beam" across the stern. Splitting the backstay might be a good option in this case - I don't know. But if you leave the backstay as is, in addition to reglassing that area, you may also want to look into installing a horizontal backing plate on the inside of that section since it's already weakened.
PS - Have you been flying a monster spin in 20 knots?
Last edited by smackdaddy; 03-09-2010 at 08:21 PM.