I generally distrust strangers. Heard too many stories of getting burned.
No problem if it is someone I've met or someone with great feedback.
This ^^^
I've also shipped low-dollar items to new folks on the site... After all we all have to start somewhere.
I find myself doing shipping more and more even for larger stuff. It's simply easier to get to the post office on my schedule than try and coordinate two busy people's lives and deal with traffic (normally) to save $8 in shipping.
I don't mind buying guns and having them shipped to me. That's why I have a C&R.
When I'm selling I do like to know there's a real person behind the deal. If it was a regular member with lots of feedback I probably would, but a newer member would have to be face to face.