So I just bought two new self tailing winches from West Marine because they were buy one get one free. I have not received them yet, but am trying to plan how I am going to install them. I currently have bronze #20 barlow winches and got #15 lewmars. The new ones are a little bit bigger. 

Right now my plan would be to remove the mounting plates for the current winches and take them to a metal shop to have them remade with the correct diameter plate. After googling other solutions I saw that one website will make these for $450... which is a little much for a couple brackets. 

Or take the brackets off and weld a new plate on top and drill new holes, this sounds the easiest

This is the only way I can think of, so does anyone else have experience installing new winches on their W28?

“…Or take the brackets off and weld a new plate on top and drill new holes, this sounds the easiest…”

If you are replacing the sheet winches adjacent to the cockpit, your statement above is the way to go.  Back in 2006, I replaced mine with Anderson #46ST/two speed winches.  I took one of the new winches to a machine shop, which created a new SS plate that fit the new winches; this new plate was then welded on the old plate with the appropriate new fastener holes.  I then secured the re-designed winch plate back on the vessel with strong backing plates.

I also bought the 2 for 1 getting Lewmar 40 Self tailing. My old winches are mounted on round wood mounts that go from the cockpit up to the coaming. Has anyone mounted winches with wood screws I dont see any through bolts

Thanks

Greg