As advertised, our Freestyle leaked oil from the Drain Plug.  There's four possible problems:

1) Drain plug was loose
2) Drain plug threading on the pan was stripped
3) The pan was cracked or compromised around the drain plug
4) The leak was somewhere else and the oil adhered to the drain plug, making it look like the culprit

To get started, we need to look at the drain plug; so, out it came along with the oil.  As you can see, the drain plug is in good condition, it looks like at one point it was replaced in an effort t

Existing drain plug, threads look good

o remedy the problem.  Once oil dripping subsided, I threaded it back in and the bolt wouldn't tighten, so we have a problem with the threads in the pan.

Now that we know the problem, here are the possible solutions:

1) Fix threading on oil pan
2) Replace oil pan

A replacement oil pan with gasket and new drain plug would fix the problem, no doubt.  After 10 or so years, it's not unexpected for the gasket around the oil pan to erode and fail, so I might be fixing another problem yet to happen.  A new oil pan comes in at $240 (from rockauto), maybe fixing the threads is a viable option?

New, self-tapping drain plug, notice the tapering

The easiest way to re-thread the existing hole would be using a slightly larger drain plug with the same thread spacing that's hard enough to cut into the pan's existing threading and make new threads.  It would also be nice if such a drain plug was slightly tapered, to make starting the cutting process easier.

Thankfully, such a thing exists at your local auto parts store: a self-tapping drain plug.  The plug also included a nylon washer improve the seal, but I could feel the new thread being cut and new new plug has seated firmly, making the washer redundant.

New drain plug, nestled snugly in its new home, sans dripping!

The slow drip of the remaining oil in the pan provided a perfect cutting lubricant and, taking our time, the new bolt was lined-up and twisted into place.  Adding some oil, we found no leaking from the drain plug.  That fixes leaking due to reason 2 above.  Looking at the pictures, the gasket seal around the oil pan still might be compromised given the accumulation of oil or we could have leaking further up the engine.  Before setting the car down, the accumulated crud will be removed to make it easier to see leaking from other areas.  For now, until we see more leakage, the worst of the problem has been solved for about $4.

The stripped drain plug wasn’t entirely bad news.  It was a signal to me that the car endured many oil changes over its life.  Maybe the mechanics weren’t careful to properly tighten the bolt or maybe they did and the threads simply wore out.   When I removed the oil filter (more on oil later), it was properly tightened so odds are the drain plug was done correctly as well -- meaning that the threads simply degraded over time.  In any event, a high-mileage car with evidence of regular oil changes is better than one with an underused oil drain plug.