Here's a simple tip to take the pain out of draining oil on the older tractors that have the drain at such inconvenient places. My tractor has a close fitting mower deck and it's impossible to get any size drain pan under the block when changing the oil.
Use a section of PVC rain gutter under the engine to direct the old oil out to the side into your drain pan after removing the plug. The same gutter works great when placed under the side mounted oil filter prior to removing it. You could use aluminum too, whatever you may have a section of.