Have you priced the ignition parts? Only made for 5 yrs ,not going to have the parts availability of a 2 cylinder. Nothing wrong with the motor itself. Just too many model specific parts. The 2 cylinder is just as good and cheaper to maintain.
I have that boat. the weight is fine as the boat is rated for either a 85/90 hp motor. Those motors were around the 305 #s so I would look at your prop design. Is that the big foot or whatever they call it now.
that's pretty common for the middle cylinder to be damaged on those. There was a service bulletin for the peehole to be re located to the top of the block to prevent that. Is that Done? try a different gauge, or pull the head off
Does that have a recoil starter on it. Those motors are pretty stout to pull. Check all your electrical connections. Make sure they are shiny clean the grounds on the block also.
buy a different motor. Converting it to a tiller is going to be expensive by itself. Then you have the lower unit problem which is a known issue on those motors.