There's no such thing as "too far" except to the eyes of others. To you biking in the rain and haircuts is somehow too far, and that's fine. If all you can give yourself is a bowl haircut, you probably are better off letting someone else do it. Maybe for you, biking is not feasible because you live too far away or you have super dangerous highways. That doesn't mean that anyone else is "taking it too far" by biking in the rain.
To quickly illustrate why asking what is "too far" for someone is entirely a pointless exercise, I'll answer why I cut my own hair. A couple of reasons, really. There aren't many options where I live and I get anxious about having to "go" somewhere to get it done when I find I can do as good a job or better. See? Dig deeper and you can see other's justification rather than judging them on the surface. Save money is just a side benefit. Not once do I feel deprived, anxious, or upset that I'm cutting my own hair.
In my own head, I can conjure up ideas that I think are "too far". But again, a completely pointless exercise. If the activity doesn't kill or seriously harm you in any way then it's probably not "too far". Living in a tent/truck/other unusual place for our modern world would be too far by my standards, but maybe not the person doing it.
The only thing I may agree with you in is that the word "badass" may be a little misplaced since badassness is also relative. The person doing the activity or living a certain way usually doesn't see themself as "badass", yet they know others will since it isn't the norm. I agree that if you're depriving yourself to save money or just to look like a badass, you're doing it wrong. The mass majority aren't doing it for these reasons though. As I said before, go beyond face value.
