Hey Brad, sorry for the delay - stereo plugs, both 1/4" and the mini 1/8" ones, are built with one more contact than mono ones - these contacts, where they slide into the mating jack, are called Tip, Ring, and Sleeve. A mono plug only has the tip and the sleeve. (The sleeve is the main, longer part of the connector - the ring, for stereo connectors, has an extra insulator separating it from both the tip and the sleeve of the connector.
The Tip is the pointed end of the connector, that's why it's called the tip. Right behind that, if the connector is stereo, is the Ring - this is only about 1/4" of the connector's length. The rest of the part of the connector that slides into the female jack is called the Sleeve - Behind that is the Body of the connector, which is bigger in diameter.
So-called Stereo phone connectors are not necessarily USED for stereo - it just means that they have this extra contact, for a total of 3 contacts instead of two. If you use these connectors for stereo headphones, the tip and ring would be used for left and right channels as I mentioned above, and the sleeve would be used as a ground that is common to both channels. That's why it only takes 3 wires for stereo headphones - ground can be common to both channels, so you only need one ground.
The term, TRS, is a shorter way of saying "Tip, Ring, Sleeve" - it just means that the connector has 3 contacts instead of two. These connectors could be wired in ANY combination, but the audio standard is set up in two possible ways depending on how the connector is being used.
If used as a stereo pair, such as headphones, the connections are (memory trick here) Ring/Right, Tip/Left, and in ALL cases the sleeve, or body, is ground.
The exact same connector can also be used for ONE channel of a system using BALANCED audio connections - in this use, the Tip is wired Hot, the ring is the low side, and again the body or sleeve is ground. These terminals, if used in a cable that changes from phone to XLR, would be wired as shown in the diagrams in that Rane note I linked.
To (finally) answer your question, if you use 2 conductor plugs then you need 2-conductor jacks. Same way with 3-conductor. The plug needs to match the jack.
There are rare exceptions to this, but this post is already too long - ask again if you start messing with insert jacks on your mixer... Steve