I am not an expert on status match so I can't speak on that but obviously you should pursue it if possible.
C+ happens almost always. For PM/DM it's nearly instant and for SM/GM it's a few days before or at the gate. I think you will get that like 80%+ of the time as a SM/GM.
For the life of me I can't figure out when I'm going to get upgraded. My worst upgrade route is MSN--> MSP and yet I do well on MSP --> LAX, go figure.
My main advice as not the most savvy, but savvy enough, is to get either the Platinum or Reserve Amex. It will get you so many more miles and if you have to re-earn status, it will make it far more tolerable along the way.