Actually, I think planes are pressurized to 7,000-8,000 feet. I contacted DAN with a similar question, and since their altitude guidelines are for ascents greater than 2,000 feet, they said it is safe to fly immediately after diving at a lake at, say, 6,000 feet.
The problem with answering your question definitively is that the altitude guidelines are not well studied, and there are conflicting opinions from different organizations. What follows is my take on your question, and I suspect some will disagree. I believe the countdown starts as soon as you reach altitude. In your example, I would indeed count the plane flight. Similarly, I live at 5,400 feet, and when I dive in one of of lakes at 10,000 or more feet, I take into account the elevations I encounter on my drive.
But driving brings into account another factor--unlike flying with its direct ascent, your drive may take you through a series of altitude changes and leveling off--in effect, a series of decompression stops. To my knowledge, this has not been studied at all. When I drove from Kona on the west shore of the big island in Hawai'i to the volcano on the east side, it took a number of hours to get there, with a small ascent followed by a long leveling off, followed by an ascent with a long leveling off, etc. How do you take that into account?
Divers in Colorado frequently dive in Santa Rosa, NM, and they have to drive home over Raton Pass, an elevation a little over 3,000 feet higher than their dives. The drive from Santa Rosa starts with an immediate elevation gain that is within the DAN guidelines, and then is roughly level for a couple of hours (decompression stop?) before the final climb up the pass. Technically, the drive home violates DAN/PADI guidelines, but many thousands of divers do it every year. The only one I know who ever got significantly bent after such a drive was my dive buddy for the weekend. We both drove home together, breathing O2 as we drove, running out of it at the very top of Raton Pass. The next morning I was just fine, and he was on his way to the chamber. The only difference between us was that when we got back to Boulder, I went home at that altitude, and he went to his home at about 8,000 feet. Was that the difference? Who knows?