Note that my boat had 304 Stainless backing plates under the 304 Stainless washers.
After my keel bolts were replaced with larger diameter 316 Stainless bolts and nuts, the yard reamed out the backing plates and installed new washers. I decided to get all washers and backing plates out of any water that may find its way to the bilge. I made G10 backing plates with rounded corners to sit under the Stainless backing plates.
Here is how my system works;
316 Keel bolt poking through the stub into the bilge; (you can still see traces of the old bedding compound)
3/8" thick G10 backing plate; (the red handle is an old toothbrush that I use to periodically clean the threads of the nuts & bolts)
Stainless backing plate; (after I clean the threads I work a dab of TefGel into the threads of the nuts & bolts)
316 Washer and 316 Lock washer;
The 316 stainless nut goes on top, and is torqued as tight as I can get it with a 25" breaker bar.