A couple of things you might want to do.
If the engine hasn't been run in so long that you really need to check to see "make sure it will run" you will likely need to repack the shaft. Before running the engine I'd pull the old packing out, that way you can't score the shaft by running it dry.
The trickier part is the possibility of damging the cutlass bearing. The hull
can shift shape dramatically when out of the water, so even if (and it's a big "if") the engine was properly aligned the last time it was in the water it will surely be out of line now.
How far out of line will cause damage to the cutlass bearing in a minute of operation? I haven't a clue. Maybe you can get someone else to say it's ok and offer to buy you a new bearing if they are wrong.