The point is that whether you crash in the first mile or the last mile, you still crashed on a trip. Since you can’t count 9999mi safe, and 1mi deadly then you’re realistically doing statistics on trips, then multiplying by miles but this just inflates the numbers and muddies the waters.
The multiplication by miles isn’t obviously wrong but it’s definitely misleading. It’s the kind of thing that sounds relevant but isn’t really.
If you are going on holiday, you have a time budget for reaching that particular destination. With a car you would maybe choose places within a drive of 3 to 11 hours (at highway speeds), whereas a plane would maybe be between 1 hour and 16 hours. But then a longer road trip might also be more dangerous.
Current commercial helicopter transfer service from Manhattan to JFK (about 15 miles) is scheduled for about 5 minutes:
In your second example, you're missing the point. People tend not to take longer road trips out of a safety budget but a time one. With a limited vacation time budget, time spent travelling (unless that's the point of the vacation) is lost. Auto-based vacations tend to be closer to home.
All things equal, people tend to budget about (one-way) 10 minutes for shopping, 20 minutes for commuting, and about 3--12 hours for holiday travel.
By foot, that translates to about 1/2, 1, and 6--36 miles (at 3 mph).
By bike, about 2.5, 5, and 45--180 miles (at 15 mph).
By auto, about 5, 10, and 90--360 miles (at 30 mph, typical aggregate speed).
By high-speed rail, 25, 50, and 450--1,800 mi (averaging 150 mph).
By plane, the shorter trips don't make much sense, but 1 hour travel will get you 150 -- 500 miles, 6 about 3,600 mi (continental distance), and 12 hours > 7,000 mi (intercontinental).
Numbers are rough, but for ballpark comparisons should work.
People didn't begin travelling continental / transcontinental distances for holiday or business until air travel was widespread, cheap, and safe. Where exceptional travel was absolutely required it was undertaken, though until the age of steamships, very very few people undertook ocean voyages of more than a few days' duration. Crossing oceans took weeks, if not longer.