Re: lower unit reseal
No "goop" is necessary for the parting line between the gearcase and midunit. The O-ring is sufficient seal if the surfaces are clean and in good condition. However, a thin coating of RTV silicone or anaerobic sealer could not hurt.
As I remember, the lower drive shaft bearing sets the gear lash and there are NO shims. The cup simply sits in the recess of the midunit (second photo).
However, there are different shims for the forward gand reverse gears on the propshaft. The thickness of these set the lash of both gears with the pinion. More later.
The pinion must be set with a (according to the factory) NEW pinion nut. However, you can re-use the old nut if you either squeeze it slightly in a vise to deforem it again or you re-stake three sides with a punch. Either method deforms the threads slightly, making it a self-locking nut. Again, If I remember correctly the pinion nut must be torqued to 80 INCH pounds. This overcomes the resistance of the deformed threads and sets the pre-load on the two tapered roller bearings carrying the drive shaft.
Now, back to gear lash: Most Chryslers of this age were set up loose, according to an old Chrysler mechanic I knew. You may very well be able to replace the whole gear pak into another gearcase and still be within tolerance. When you do, spin the shaft without the waterpump or seal so you can "feel" the gear mesh. If it is smooth without any grumbling or grinding, it will probably be good.
And, as an aside, the two piece lower unit while very nice looking is not nearly as good as the one piece. If you find a one piece engine that is trashed, for cheap dollars, you can transplant everything of yours onto the one piece midleg and lower unit. You will then have a better performing engine with a better choice of props AND about 2-3 MPH more top end. I alreade did this on a 90 on the boat in the avatar and proved that it does indeed get 2-3 MPH more.