What's the first thing you know?

I changed the oil, if you can call it that, in my flathead 6 last weekend. I say "if you can call it that" because it was more like molasses than motor oil... thick and black. And it barely registered on the dipstick.

Before I changed it, there was an oil leak. Not much, but a leak on the driveway maybe 6 inches long.

After I changed it (and luckily, I decided to leave an oil catch pan under the truck) I have a river of oil dripping to the ground, gravity being what it is. Now this flood didn't start immediately. A few hours after I changed the oil, and ran the engine, there was one drop in the pan.

Yesterday, I noticed the flood being caught in the pan.

I was checking for the source this evening after work, and I believe it's coming from the bottom of the oil filter. Not from the top which I removed to get at the canister, but from the bottom, which I did not touch.

Being new to all this flathead stuff, I was wondering:
1. If it's possible to put the oil canister in upside down?
2. If oil thinner than molasses may have found its way past gaskets I'm not even aware of?
3. If it's inadvisable to ever change the oil?

What say ye, oh oracles of Ford flathead wisdom? And stuff...