A few years ago in Orlando my student and I lost about 1200 feet in a downdraft in IMC conditions while getting vectored for an ILS in a Cessna 172. The altimeter just dropped from 3000 feet to 1800 in about a second. We slowly climbed back up and I requested a full stop.
A couple of months ago, one side of the engine cover on our Piper Seneca flew open in flight, I told the student to power it down to idle and we did a simulated single engine failure landing. After landing, we secured it and took off again for our training flight.
On my MEI checkride my examiner said, "I gave you your multi commercial last week, lets have some fun today". After the checkride, he gave me a critical engine failure in a Piper Aztec with me in the right seat on a partial panel ILS approach. Since the hydraulic pump is hooked up to the critical engine I had to pump the landing gear down and the flaps down using a handle while I was under the hood flying a single engine partial panel ILS. Nothing yet has tested my skills like he did that day. I passed my checkride and had a sense of accomplishment that I didn't bust the approach. Now I now what an examiner's idea of "fun" is.