Does your engine have "Selectric" trim? In other words, hydraulic trim built into the motor mount?
If yes, run the trim bow down (engine goes full up). Is there room to place blocking under the oil pan or front pulley to support the engine & remove the mount?
If no trim, can you hoist the engine enough to remove the mount?
If you feel like there won't be enough room to work, then pull the engine. Just replacing a freeze plug should be quick after you have access. Probably can work it with engine lifted but inside the boat.
Removing the engine in theory can be done without removing the intermediate drive but the outdrive needs to be off or blocked so it isn't placing any weight on the housing.
I have never done it that way, I always pull the engine & intermediate as an assembly. Probably time for a new transom seal.
Most likely the drive shaft splines to the engine coupler have never been greased & now is the time.