As Dan said the whining may be caused by the loose strut and obvious misalignment. You might not need to replace the strut itself once you find out why it is loose. Find the cause, fix the problem, re-install the strut if not bent and replace the cutless bearing. It will be easier to install the new cutlass bearing on a press when the strut is removed.
Since you mention leakage, you might want to replace the packing gland as it has probably suffered from the misalignment and vibration of the shaft. Easier and less worry when doing with boat out of the water.
After strut and shaft are reinstalled and bolted on the tranny, with engine in neutral make sure the shaft is turning freely. Once in the water, check engine/shaft alignment. Chances are with the problem you're describing you will need to re-align.
Don't know if it's the same on your boat, but on mine I can take tranny out without touching the engine. If it's the case, I would try the boat and see if tranny is operating correctly without that whining noise. PO being careless enough to tolerate such a problem, I would change the oil in the tranny before using the boat, or at least check the level.
You don't specify the make of engine or model of tranny, but if you need to, there is an excellent shop in the Fort Lauderdale area. I believe it's called Marine Transmission Service.
Good Luck