Re: 69 25 hp Evinrude water in gear oil
The gearcase head is the prop shaft seal. I have changed out the seals in one, but needed a dremmel tool to get it out. replaced seal and jb welded the washer in place. But I had the gear oil running out. No leaks.
The seals are designed to keep grease in, not water out. It's just the way it's designed. If you get the Sierra gearcase seal set, the seals that you need for the gearcase head should be in there.
As far as it jumping out of gear, you have a worn clutch dog. A temporary fis is to turn it around, then all you have to worry about is it jumping out of reverse instead of foreward.
These are good motors and easy to maintain, but age is getting to them and repair parts sometimes are more than the motor is worth, so one has to be creative and improvise.
I have 2 (one 20HP and a 25HP) and would get another with a frozen powerhead in a minute, ( I've got 2 spare powerheads looking for a home)