My $0.02, with the Tyndall F-22 disaster, the military has too much red tape and rules that some enterprising O4 couldn’t take the initiative to take a GPC, rent a bunch of flatbed trailers, hitch up the jets, find a few truck drivers/ jet maintainers to go along, and convoy them to Warner Robins or somewhere outside the hurricane zone. So the jets were left in place at a damage cost of X amount. The culture doesn’t allow for outside the box thinking and rule bending.
What you describe is a recipe for a disaster far worse than what happened at Tyndall.
F-22's aren't some used Hondas you can just throw on a car transporter a U-Haul trailer you can just hitch up to your truck, they require specialized handling equipment not just to transport long distances over land but it also takes
significant planning and support as well. That includes everything from route planning to ensure they can physically fit along the route without hitting every telephone pole, stoplight and overpass along the way to pretty strict physical security requirements needed 24/7 for every single jet along with making sure the transport doesn't run out of gas to rest requirements for the personnel.
For all the lamentations about red tape and rules there is ample good reason for them in cases like this, so you don't have some bright idea fairies wrecking an F-22 in a ditch on I-65N while trying to get around all the other hurricane evacuees followed by folks taking Raptor souvenirs that end up on eBay 7 hours later.
By far the two best options for aircraft and ships is to physically get them out of the way if able or secure them where they are if not.
