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I probably should have taken the time to go ahead and figure out how to loosen the housing drain cover and replace the O-ring.
That drain cover on the filter housing serves only one purpose: to make the oil change cleaner, with less mess from spilled oil. When the drain plug comes off, you should drain the oil out of the housing before unscrewing it off.
If the drain pug is "stuck", unscrew the whole housing and dump the oil out of it. Granted, you will spill some, but still, there is no reason to remove that drain plug just to replace the rubber o-ring.