Re: 15 hp - no compression on one side
If it were me, I'd check and make sure the head is flat by placing it on a pane of glass with 400 grit sandpaper on it and rubbing the head in a figure 8 motion until it is flat. If the head is warped, that could be the problem with the head gasket going bad.
As to the 88 psi thing......... Where did this exact figure come from?
My 50's 7.5hp OMC motors consistently run with 80 psi and knowledgeable people with reliable gauges have motors running good with even less, some down to 65psi. Even older, smaller hp motors consistently run great with 60psi. on one or both cylinders.
I have found the rope start motors giving lower compression readings of about 5 or so psi lower to be normal. You just have to pull them over a few more times to get the highest reading. Not 15psi difference that I've seen, but I guess everyone's arm strength varies.....
I do believe a newer 15 hp johnson would have higher than 110 psi in good shape, although it would run ok. with less. My '56 15hp I believe even has 105 psi. well used, compared to my highest compression '57 18 hp with 125 psi on both cylinders. MY '99 johnson 25hp purchased new only has 125psi as well.
just my 2 cents.....

I think your motor has a good chance of being a really nice one.
Good luck,
JBJ