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Outer transom plate leak

I have a reoccuring problem aside from the others I mentioned in an earlier thread. The boat I have, a 1992 Reinell 2000elite 20 foot cuddy, leaks water at the bottom of the transom. It comes in just above the lower drain where the exhaust exits from the inside to the outside. Basically it comes in where the inner transom bracket plate on the bottom is attached.
I found that the mounting nuts off the plate were rather loose, so I tightened all of them, and this significantly reduced the amount of water that was coming in from a small stream, to just little drips.
My question is, having never worked on the outer transom plate of any boat before, is it possible to back off all the inside mounting nuts enough, so as to pry the plate loose just enough with wooden wedges so one could shoot some real good marine caulk up inside?
Not gobs of the stuff, but just enough to act as a gasket, I sure would hate having to dissassemble the entire out drive and remove the outer plate just to put a gasket on when a little bit of caulk would do.
Is this possible, or am I just thinking wishfully? Thanks in advance for the advise.

Rick
 
Is the plate #39 installed? (See lower left of pic)
or just washers and nuts?
Have seen that to often to be missing.
You may have to remove the whole assy and 'redo' the lower part if rotted out.
 

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The plate #39 is installed and the nuts are marine stainless vinyl lock nuts, but they were loose, there is no rot in any disernable part of the lower transom. Which is why I was wondering if it was possible to just back the nuts off just a tad all the way around, so the outer plate could be gently pryed loose, even if it was just a 16th that would be enough to get some caulk up in there. If I can get more than a 16th that would be great, but a 16th would do if possible and would not damage any of the internals. Thanks for the reply...Rick
 
I'm afraid the only way of repairing that I may recommend, is to completely remove the transom assy and have your transom 'straightened out'.
The main seal is a rubber string going in a groove in the outer assy and this may have been damaged as well.
 
Sooo, you're saying that the caulk idea is a gonner, no possible chance that may help. The thought of removing the outer transom assy is not pleasant..., but i'll do it if that is the only way..., but not this year, too many other things in the way. Thanks
 
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