OK, well first start slowly….You really want to be sure you have something solid to work with before investing money and time only to find out the powerhead/gearcase is worn out/NG….
Start with a compression test, this thing might be difficult to rope over without an electric starter, please make sure it is mounted on something solid, like the boat’s transom…Look at the paint on the cylinder head/block, does it appear burnt/badly discolored? If so, the engine has been overheated at some point in its life…
Next, drain the gear lube, there are two large fill/drain screws that must be removed, one might be hidden under the forward part of the gearcase bullet. Do NOT remove the small phillips screw, if one is present. This is the shift linkage cradle retainer screw, the linkage will fall down into the gearcase and you will be screwed…
In any event, have a look at what drains out….Old lube was dark in color, so this is normal
Newer lubes are a light brown/tan color…
“Milky colored” lube indicates there is water mixed with the gear lube
Raw water draining out spells trouble
If nothing drains out at all, you are in big trouble. Look for a crack in the skeg, freeze damage.
Have a close look at the whole engine, look for parts/pieces that might be missing, or broken/bent castings…
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