Above post is right on the money. The Cobra can last a very long time, due to good oil capacity and large bearings. The things that should be looked at to keep it that way:
1) filling the drive the right way, go onto the tech support page on Crowley marine and they have that all from the factory shop manual
2) maintaining the shift system...the cables must be properly adjusted but that is not the only point...
a) transom shift cable drag must not exceed 2.5 lbs measured with a fish scale, this can be checked when adjusting the transom shift cable with it disconnected at both ends
b) to do the adjustments you must have the 2 special tools made by OMC and others, to get the adjustments right
c) the adjustments start with proper shift rod height, this is important but often overlooked
d) after doing the transom shift cable you must also do the remote cable. This is needed to get equal shift stroke (travel) in both fwd and rev, or else it will go into one gear fine and grind in the other
e) there is a shifter bell crank in the pivot housing, this part is moved by the transom cable guide and moves the shift rod on the lower unit up and down. There is a pocket behind it that can get built up water deposits and will restrict the movement of it causing stiff shifting and not going all the way into gear. This has to be cleaned out and packed with OMC triple guard grease each time the drive is removed. Later model ones like yours may have a grease fitting there, use it!
f) idle speed should be no more than 600 in the water
g) ESA must work and lower the idle speed to about 450 rpm
h) engine should be in good enough tune so it will not stall running at 450 momentarily
i) the remote control should not be sloppy with lost motion, if so it will affect shifting. If the boat has an original OMC control (they were pretty good) it may be worn out by now.
It should not shift stiff at all, should not grind going into gear as long as you shift firmly and not slow and it should not jump out of gear (most important because this will round off the clutch dogs and result in a lower unit rebuild).
ESA must actuate when shifting out of gear on the water, it will not on land due to not enough pressure on the prop.
PS mine was gone through about 15 years ago, before I bought it. All I have done is have it resealed once. Same gears, same cable etc. I adjusted it once in 2013 because the remote cable adjustment and shift rod were both a bit off. Still shifts fine. I actually prefer it to the Mec Alpha, as long as I can get parts I am sticking with the Cobra....