「Wood」with「doubtful condition」may refer to a sleepy state of both a client and the service provider, with the latter resting her head upon the woody as a sort of PILLOW after tiring from performing services in that location. In any case,「woody in some doubtful condition」implies softness, and not working or functioning at full capacity.
Any「woody in doubtful condition」due to infection might cause the person to REST ONE'S HEAD UPON SOMETHING (perhaps both heads) and require the use of a PILLOW of some kind, especially if near death and lying down most of the time. Note the right element is comprised of「erection surrounded, with bent penis」that in Chinese meant「to move on to the next one, to go out and leave alone」due to increased risk or non-functionality.
Formerly, what are today called pillows of the Japanese upper classes were more of a wooden HEADREST rather than sacks filled with soft stuffing. The device held a lady's head off the floor after obtaining that extra-special coiffure, in the same manner as a concubine's head was kept off the floor by a woody, but frankly, it seems that sleep itself with a wooden PILLOW may remain a「doubtful condition.」
In any case, some members suggest that「tree, plants」in a「weakened, doubtful condition」may have referred to leaves or softened, rotting wood from the forest floor stuffed into a sack that might have made a more comfortable pillow for those of us in the lower classes who never minded the smell anyway, but also may have contributed to waking up with a few small critters in one's hair.
Today, modern PILLOWS are often full of critters, too (mites). Note that it is generally not the bugs themselves that cause allergies, but rather the material they leave behind after feasting on your natural body oil and sloughed skin all night. Japanese often air out their pillows and bedding in the sunshine whenever possible to counteract this, perhaps as an acknowledgement of the often「doubtful condition」of any PILLOW.

External source definitions …excluding politically incorrect concepts and other meanings deemed offensive today; may include extended definitions, euphemisms, and mnemonics)
Chinese: pillow; to pillow; to rest one's head
Japanese EDRDG: pillow
Unihan extended: pillow