I'm not sure what the new car lots look like where you're at; but, here in NC you can buy any brand white regular cab pickup with a Reading box on the back that you want....other than that, good luck. My brother in Michigan totaled an Escape and needed a new car last week, he saw them unloading three Edges into a local dealer, two were sold before he got in the door and he bought the third. By the time the car hauler was unloaded, the dealership was back to, you guessed it, 5 white work trucks with utility boxes. They say that you can see the pile of Superdutys/Expeditions outside of Kentucky Truck Plant from the space station with the naked eye. I don't think things are going to be back to normal for a while, you might be stuck occasionally driving two vehicles to your destination.
As for "timing the market". The only way is with excess inventory. I just sold my 2007 F150 Lariat 4x4 with 200K miles for $16K!....to a dealer!!! I still have a 2013 F150, 2012 Mustang, and 2020 Expedition for 3 drivers...so, we can ride out the high prices for a year or two.
Good luck.