Full transom swim platform install

I will be installing a full transom swim platform on my V20 cuddy in the near future. What type of sealant should I use to seal the holes I will have to drill in the transom (God, I hate the thought of doing that) for the bolts to hold up the swim platform brackets? Man I hope I do not get into any rot when I drill into the transom!
 
Well after hours of cleaning the swim platform, then sanding it down, and 4 coats of Cetol marine finish, I put the mounting brackets on the platform, then put in teak plugs to cover up the bolt heads. Cut down the teak plugs flush, sanded them, and then thought I would install the platform and then give a few more coats to the topside and I would be in business. Well, looks like I am just starting. I did not realize that the transom of my V20 Cuddy (I/O) is nowhere near straight. There is of course about a 12 degree on the transom from keel up. What I did not realize is that the transom tapers from the center to the ends, and the current platform/bracket configuration I have will not work. So, I will have to take the brackets off (which means my current mounting holes and the teak plugs on the top of those holes will be useless) and try to reconfigure using the current brackets. I am not hopeful they will work however because they probably extend down too far for proper mounting.

I took a bunch of pix yesterday and will post them along with a plea for help/ideas!
 
The stainless brackets for them things are outrageous.
If you can't find any other way around it, let us know and we can give you the bad news cost wise.
 
I did a little web surfing for information on swim platform installation (which I should have done first) and learned that you generally want to mount the brackets on the transom and THEN mount the platforms on the brackets. What a waste of time I went through.
 
And look on the bright side.
No holes drilled in the transom, that might be incorrect.
And look at the 5200 that ain't on your eyebrows, under your armpits, etc, etc.
 
I just hope I can get the teak plugs out without messing up the platform. I bought the platform off of ebay, and there was only one teak plug covering one out of the 4 holes the bolts go down through. When I went to pop that plug out, it popped out, but along with small pieces of the surrounding teak. Of course, I had to go and glue in the new plugs, and that wood glue will probably cause the same thing to happen--times 4!
 
First drill the plugs out 1 or 2 sizes smaller, then you can use a sharp screw driver to clean the rest out.

Go to your west marine or boaters world and buy a leanth of rail and needs and make you own brackets if yours don't fit.

I would put every thing toghter and have some one hold it up while you make adjustments and mark transom, then install.

I had to use shims when I installed my motor bracket cause it had full platform, and it did not curve around transom.
You should be able to cut a row of slats out in the middle to make up for the curve.
 
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