what does it even mean for the implication to be true ?
Here are the four types of ‘imply’:
$P$ implies $R$
- Some complex number is real implies that every positive number is real.
for each $x, Px$ implies $Rx\qquad\leftarrow$universal implication
- Every multiple of $6$ is even.
$P$ logically implies $R$
- $\big(A\to\exists y\,By\big)\,$ logically implies $\,\exists y\big(A\to By\big).$
$Px$ logically universally implies $Rx$
- $x\not=x\:$ logically universally implies $\,Rx.$
(Roughly speaking, a logical truth is a sentence that is true regardless of how its symbols are interpreted. For examples 1 & 2, the context is mathematical analysis.)
$\qquad$ I am holding a pen $\implies$ It is raining outside.$\qquad(1)$
This implication seems to say that it will rain outside whenever I hold a pen.
No it does not: this Type 1 example is a synthetic implication (its specific context might be right now, in Ximending, Taipei), not an analytic implication or general truth that suggests a prediction or "will / will not".
me holding a pen and seeing it does not rain does not prove that the implication is always false.
It does: your description means precisely that implication $(1)$ is false.
Which is not to say that it is logically false: clearly, it is true in some other scenario/context.
In contrast, the implication
$\qquad$ "I am holding a pen and every empty-handed person is holding no object implies that I am not empty-handed"
is logically true (Type 3 above). When you're writing the following and wanting to analyse implications across varying contexts, you are probably thinking of Types 2-4 above, whereas vacuous truth in the context of Type 1 is really just a matter of definition:
the implication is always false
the implication to be true, for the times when I do not hold a pen
the implication would be true when I do not hold a pen
anytime I hold a pen, the consequence in the implication will be false.