Some additions to the title: I stumbled over this problem going through my measure theory lecture notes; the author explicitly mentions that he leaves $\infty-\infty$ undefined. I would like to know what goes wrong, if I would define $l:=\infty-\infty$ for $l\in\overline{\mathbb{R}}$.
I tried to derive contradictions by playing with arithmetical rules in $\overline{\mathbb{R}}$ but couldn't obtain a contradiction.
Here's an example where I merely try to obtain a contradiction by assuming that $r:=\infty-\infty\in\mathbb{R}$ (as opposed to $\overline{\mathbb{R}}$).
\begin{eqnarray*} & \infty=\infty\\ \Rightarrow & \infty=\infty+2\\ > \Rightarrow & > \infty+\left(-\infty\right)=\left(\infty+2\right)+\left(-\infty\right) > \end{eqnarray*} an here the attempt breaks down, since this extended addition doesn't have to be associative, so one can't conclude \begin{eqnarray*} \Rightarrow & r=r+2\\ \Rightarrow & 0=2. \end{eqnarray*}
EDIT A lot of people gave me answers in which they motivated why $\infty-\infty$ doesn't make sense. This is not what I'm looking for! Motivations are nice, but only a concrete contradiction gives certainty that it absolutely makes no sense to assign a number, or $\pm \infty$ to the above expression.
If $l:=\infty-\infty\in \mathbb R$, then $1+l=1+(\infty-\infty)=(1+\infty)-\infty=\infty-\infty=l$, contradiction.
If $\infty-\infty=\infty$, then $-\infty=-(\infty-\infty)=-\infty+\infty = \infty-\infty=\infty$ and imilarly if $\infty-\infty=-\infty$.
So each possible choice of defining $\infty-\infty$ as a value in $\overline{\mathbb R}$ produces contradictions to the (desired) proerties of addition such as associativity and commutativity, as well as to $\infty\ne-\infty$.
You may have better luck in a one-point compactification of $\mathbb R$ where $\infty=-\infty$ holds. But that structure is unsuitable as a tool for measure theory.