I know what you're talking about pirate, when my wife takes the boat alone it usually ends up looking like that when it comes home. I've made her paranoid about blowing baffles.
I've spent a little time examining my boat on the road, even used a pressure gage to get a feel for how it changes. I now adjust the pressure very little. I've gotten to the point where when I'm concerned, I let 3 seconds of air out of each chamber when I take out and put 20 pumps with my k pump in when in the water at the put in. Most of the time I do nothing, as long as the temp swing isn't more than 20-25 degrees. That typically does it for me but we don't have the elevation changes you Coloradans have, typically 2-3k is max on my trips.
We do see massive temp changes though, often in the summer it can be 45 degrees when we leave the house in the morning and 90+ when we get to the river (on longer trips). That's when I get more paranoid and deflate a little extra some where along the way. I do let air out at home when it's going to be sitting for a while, it can get very hot in my garage and its just nice to not wonder. I do things in that 3 second blow off, 20 pump increment. So If I let extra air out, it's another 3 seconds out, that way when I'm to the ramp I can tell someone to put 20 or 40 pumps in, which ever is required. That ratio just works well for my boat and gets other people "involved" at the ramp.
Yesterday's gone on down the river and you can't get it back. - Agustus McCrae