About having no bookings yet, that part was always sketchy. I went 15 years ago to the US for a 4 week trip and had only lined up the first hostel for a few days, the rest I had not planned yet, luckily got no questions but worried about it back then already… Guess this is a thing of the past now.

Huh? You base “was always sketchy” on your personal feelings doing that yourself 15 years ago?

I really don’t see what’s sketchy about not booking four weeks ahead.

I’m more of a planner, but my grandparents get in their car and drive through and around Italy without a single stay pre-planned.

I don’t see how that’s suspicious or sketchy at all.