If you raise the front end of your vehicle, and support with jack stands, you may not be high enough off the ground. Crawling under, with less than 12", does not allow you to be in a good position, or use longer tools with more leverage. Sometimes, reach and access is limited when you're trying to use power tools. When you have the vehicle up on a lift, you can stand under it. This allows you to plant your feet in a wide stance, get your body behind the tool, or maybe use power tools. Think about an impact tool. You may also need some sort of universal joint to give you the correct angle.
I would also worry about the condition of the threads after you get the drain plug out.