Al Cruzar/Cruzando

[Bobbert]

You should have been much more careful crossing the street
Which one(s) is/are correct or incorrect and why.

Deberías haber tenido mucho más cuidado al cruzar la calle
Deberías haber tenido mucho más cuidado cruzando la calle

or

Deberías haber sido mucho más cuidadoso al cruzar la calle
Deberías haber sido mucho más cuidadoso cruzando la calle

Thanks in advance for any input and/or explanations you can give me.

[poli]

Tener cuidado is much more common and it means be careful. It is often used in a command as in a parent and child/

Ser cuidadoso much less used, and its meaning is slightly different. I think it often means to be cautious. Then there's also estar cuidadoso....:D

This answer is coming from a non-native speaker, and a definitive answer should come from a native speaker.

[AngelicaDeAlquezar]

I mostly agree with Poli. For this kind of situation, it's more commonly used "tener cuidado", which means to be careful or cautious.
"Ser cuidadoso" is more associated with being attentive rather than with being cautious. That said, both sentences work well in this context, because here, being attentive is as valuable as being cautious. :)

As for "cruzar" and "cruzando": We would use "cruzar". I'm not sure I can explain it very clearly, but if you have any questions, let me know. :thinking:
When you use "-ando"/"-iendo" endings, you think about performing simultaneous actions. Here we wouldn't think being careful and crossing the street are two distinct actions, because being careful is rather to have a particular attitude; it hardly counts as doing something at the same time you are crossing the street. :D

[Bobbert]

Thank you, poli and AngelicaDeAlquezar. That clears it up for me.