I'm going from memory here (always dangerous), since I'm not in my office, but I can tell you this much:
1. The top terminal of the regulator is connected to the battery, so it should have the same voltage as the battery. The one next to it is connected to that terminal through a heavy wire, so it should have the same voltage.
2. The bottom terminal is ground, so there should be no voltage on it. If you mean the second from the bottom, (which may be the bottom wire in your figure; I can't see), then that goes to the generator, so 14.5V with the car running sounds good to me. Since your battery is very low, the generator will be going at full output. Only problem I can see is that the generator output is connected to the battery through a heavy wire inside the regulator, and I can't see a 2.7 volt drop along that wire. Might be a bad connection at the regulator or internally. Possibly the cutout relay isn't closing.
3. The next couple of problems simply sound like the column switch is hosed. (Sorry for using the high-level technical terminology.)
4. I think you've found the brake light switch. It operates on hydraulic-line pressure. This is much more complicated and less reliable than a switch connected to the brake pedal, so naturally that's the way it was designed. It simply breaks the circuit to the brake lights, and is hot when the ign switch is on.