As stated above, the Upgrade occurs based on the LOWEST status of any member in the record. Therefore, if three of you are booked and one is not an elite member, than no one will be upgraded. LAX-MSP can be a hard flight to get upgraded. I have only done it in the morning. Generally it is a 757 so there are more seats, but there are generally more elites also.
Jamito, I do the same thing. If I see someone that I think would benefit OR that I would like to sit next to I ask if an upgrade is available and get them Upgraded. I generally know if first is full before I ask someone though. I was only denied once and that was DTW-ORD, the agent said Oh yes, I have one seat left. But as she was typing it disappeared. They had just canceled the later flight to ORD and were re-accomodating and the seat she was trying to give my companion was taken at another gate to a CXLD passenger. That most certainly is fair.
In the summer the flights are generally full, but if you ask early enough on most routes they don't fill the cabin till at the gate.