I have done a few of the things you list here, like hitch hiking VERY long distances, from Rio to Salvador, Bahia -by car in one go 18 hours, it took us two days to get there and it was the truck drivers who would give the best lifts... thing is, in those times, even in the 80s, things like this weren't THAT outrageous or even daring...
I wouldn't feel comfortable with Sarita doing that these days anywhere, and, of course, there are always chances of something happening, and there is no way to filter, or else Ted Bundy wouldn't have had the success rate

but those days people weren't as ....can't quiet find the word here.... but in general there was most trust and I never had anything terrible happening to me whilst hitch hiking anywhere ( I have done in Europe in the 80s and in 1991)
I also did the grabbing a bus, (wouldn't have done in the Middle East or anywhere in Asia though, Maureen !!!!!) any bus, here in London when I first came (1989) and here, again, I would not do it again in this day & age, I have even paid expensive taxis when Sarita had to rehearse in South London until late, so she wouldn't have to wait in bus stops, or even get in the bus late at night....we are lucky our area is very very good and we live very near the train station....but still, the way things are happening these days in this city, I usually don't sleep until she gets back....she is very good at calling me all the time, but still, I can't sleep until she gets home...
But this kind of thing I don't think of as outrageous...maybe daring or like my dad would say "tempting fate" he was always against me hanglyding which was something I always wanted to do...but didn't, because even in my worse "crazy" times I always respected my dad's wishes
As outrageous, we used to do something that when I see young people doing it these days, I think how stupid we were and how ridiculous it must have looked and feel to others, things like making noise in the underground or trying to provoke reactions....
I know I always wore clothes that didn't quiet conform with fashion, to my mother's desperation LOL, but most was my grandmothers' (both) clothes, shoes & hats, so my mum would complain but my grams loved it that I wanted to wear them... but one really outrageous was a period of about 3 months in which I was going out with a quiet well known musician and with one of the other guys' girlfriend, we wore ballet clothes and shoes to every gig, even went shopping mid afternoon dressed up in tutus and point shoes

we did have a good time though !!!