I know that it is best to use the drain plug, but there are times I
hate crawling on the floor or sometimes it rains or in the winter it
is very cold.

I saw at sears an air operated oil extractor that has a ridgid
dipstick tube. It can also remove transmission fluid without taking
off the pan.

Would the life of a vehicle be shortened by using this method? By the
way the item I looked at was made by Mity-Vac and held 8.8 liters. You
use it with your air compressor.