depedns on the boat... if access is good, it's easy. if the stuffing boxes are buried somewhere witha bunch of stuff in the way... it's a major PIB. Vee drives are worst since it's under the engine!
get the flexible cork screw tool to dig the old stuff, it's much easier.
make sure your bilge pumps are working.. you'll need them although it's nothing to panic about. your standard 2000gph pump should easily keep up. also, consider using the goretex material, much easier to install as you dont' need grease and its virtually drip free.