I'd like to see them meet sooner rather than later, so their relationship can develop, and we can see how Logan and Poppy will react away from the letters.
I would rather them meet sooner than later because it would let us know how Logan actually thinks if her as a real person not just someone he talks to in their letters. So I pick the second option.
I think I'd rather them meet sooner than later. I love the idea of this story so far and I really like the importance the written letters hold and how they've both connected by them. However I'd like to see how their relationship will develop once they meet face to face, so my vote is that you go with option two/plan b :-)
This is such a great story, omg. I get way too excited whenever you update. It feels like I'm reading letters between two actual people. Keep it up! c: