Nice question, here's one possible interpretation.
Let $W(l)$ be the amount of words/equations/whatever you can fit on a row of length $l$ (in whatever units suit you). $W$ depends on how wide you write your letters. Let $H( r)$ be the number of rows of text you can fit in a column of length $r$. $H$ depends on how tall you write your letters.
Consider a piece of paper that has dimensions $a\times b$ (with $a,b$ in the same units as $l$ and $r$). Suppose WLOG that $a \geq b$.
When orienting the paper in landscape, the amount you can write is $W(a)H(b)$ because you have $H(b)$ rows each with an amount $W(a)$ of writing. In portrait, the amount you can write is $W(b)H(a)$. So our decision rule is: choose landscape if $W(a)H(b) > W(b)H(a)$.
Let's further assume that $W$ and $H$ are linear in terms of their respective arguments, i.e.
\begin{align}
W(l) &= \frac{l}{\omega}\\\\
H( r) &= \frac{r}{\eta}\\
\end{align}
where $\omega$ is the (average) width of one letter you write and $\eta$ is the (average) height of one letter you write.
Using the inequality from before, we obtain
\begin{align}
W(a)H(b) &> W(b)H(a)\\
\frac{ab}{\omega\eta} &> \frac{ba}{\omega\eta}\\
1 &> 1
\end{align}
So using our decision rule, we see that we should use portrait since the inequality does not hold. However, we also see that the amount we can write is the same in both cases, so it doesn't matter.
This is an interesting exercise in modeling and is instructive: by making some assumptions about your model you can derive certain results, which only hold as long as the model itself and your assumptions are valid. I'm sure someone can come along and find a better model for the amount you can write which may produce different results. For example, one assumption that I made was that the "amount" you can write in a row or column is a continuous quantity, when in reality it is probably a positive integer measured in words.