Ok so this is probably pretty stupid. I changed my oil as usual, however I had the hair brained idea I would pull the plug on the engine case to get the oil outta there. Now it's leaking.

The bike is a 2003 Fatboy

Here is a pic. Am I mistaken in thinking this is another oil drain plug for the engine? What is it? the puddle of oil is from about 4 hours.

 

One is your transmission plug.

 

It's called an Oil Gallery plug and no you didn't hose any thing up. Generally you don't pull that plug for oil change. If you are performing and overhaul on the lower end then is when you might pull it. Simply pull the plug back out and attempt to clean any debris from around the threads in the case. Careful of what you stick up there. If you use a solvent make sure you get the residual stuff out of the case. Clean plug of crud and apply some Loctite on threads and tighten securely. Done. Oh by the way, put your oil back in...

 

Thanks! Problem fixed, time to ride...

 

It's still leaking. It turns out the case appears to have a hairline crack around the bolt. When I loosened it I heard a snap, but I thought that was the thread locker breaking free.
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Am I hosed? Any ideas?

 

You can have the case crack welded but I do believe it will have to come apart. That plug is red loctited in at the factory and should have been heated to remove. This is a common mistake quite a few people make.

I would consult a few indy shops and see what fix they recommend.

 

Are you certain it is cracked? Can you visually see the crack? If indeed it is cracked you have three options: 1) Have it welded, but you may have to gut it first. 2) Apply liquid steel to the area that is cracked, but it will likely fail over time. 3) Take it to a reputable shop and have them look at it. Chances are they are gonna want to gut the motor to replace the case.
The cheapest approach would be to coat with liquid steel/JB Weld and let it cure. To do this means you need to clean the surface of any residue so it will bond.
I must admit, this is the first time I've heard of Thread Locker/Loctite causing a crack on an engine case nut removal, but I guess it's possible.