Ah, wait a bit, you'll understand.
When your hips and knees get so bad you kinda crumple occasionally when you try to get off the bike after riding a full tankful of hard mountain twisties ....
Heck, if we couldn't "trailer up" somehow neither Lancer nor I would be going, that kinda old and decrepit ....
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This towing your bike out of your open trunk idea isn't a very good one. As a matter of fact, it sucks big time .... The issues focus around the high center of gravity of the towed bike and the fact that going around a turn causes the bike to tilt. In the trunk position the center of gravity is so high that the bike tilts over and tries to hit the bumper when making a simple 90 degree turn.
This roll over from the trunk position is so severe the bike doesn't always manage to straighten back up all the way once the turn is over.
Lastly,
the Harbor Freight bike chock isn't tight enough on the front tire to support this roll over shite. There is room for the tire to slide over in the chock and when this happens any compression on the front forks wants to relieve itself and the result is a strong sideways binding condition between bike, car, chock and the front wheel assembly.
The front wheel assembly is what loses out in this scenario, you can/will warp your front wheel some during a turn/tilt over episode. This results in time spent spoke truing your front tire and whapping your rotor with a BFH and a block of wood to remove the run out of rotor and rim. And all this damage was done at barely moving speeds, I shudder to think of what road speeds would do to a front wheel (rip the sucker apart, most likely).
If you wish to pursue these sorts of ideas, try using Verslagen's trick of removing the front wheel and hard mounting the front axle ---
and try to keep the center of gravity as low as possible to keep the tilt monster at bay.
Idea is rated Dumb, Dubious and Dangerous .... don't do it unless you like fiddling with spokes, truing wheels etc