Re: 88 50hp rebored cylinder/oversize headgasket
The baffle is smaller than the cylinder and piston diameter and MAY clear the rim of the steel ring at TDC. The piston itself will not rise up far enough to hit the gasket. If the baffle clears the steel ring, then it may be OK to used depending upon if there is enough of the steel ring on the cylinder wall to support and seal.
If the baffle does not clear the steel ring, then I have no suggestions. Your engine is 3.187 bore. .020 over gives 3.207. The later gaskets are for 3.375 bore. On the three and four cylinder engines the same gasket is used for 3.3125 and 3.375 but in your case, I think the later Force gasket for the 3.375 bore 40 and 50 HP engine would be too big.
I never ran into this problem because I never overbored an early 50 HP engine.