With a similar issue years ago, i replace both as well. I purchase two cheap sockets (to fit the different size drain cocks) and modified them as to accommodate the drain tubes/pipe nipple; see pic. Handy for extraction, but even more valuable for reinsertion.
VERY IMPORTANT: On the Port side of the Block you'll find the Oil Cooler (Oil filter is attached to it). On my X22 the Oil Cooler water jacket is drained via a hose into the Drain plug. The pipe nipple on the drain plug was pointing aft, away from the Oil Cooler. Over time the tight radius making a U-turn in the hose, kinked and pinched shut. Thus sediment was pulled into the Oil Cooler and never allowed to drain. Eventually it plugged solid, and I had to replace the Oil Cooler. THEREFORE, when I replaced the drain plug, I made sure to point the water hose nipple forward and cut the hose to the proper length.
-WNF-