The following is from "An introduction to measure theory" by Terence Tao.
Motivated by this, given any collection $(x_\alpha)_{\alpha\in A}$ of numbers $x_\alpha\in [0,+\infty]$ indexed by an arbitrary set $A$ (finite or infinite, countable or uncountable), we can define the sum $\sum_{\alpha\in A} x_\alpha$ by the formula $$\sum_{\alpha\in A} x_\alpha=\sup_{F\subset A,F\text{ finite}}\sum_{\alpha\in F} x_\alpha.$$
Note from this definition that one can relabel the collection in an arbitrary fashion without affecting the sum; more precisely, given any bijection $\phi:B\to A$, one has the change of variables formula $$\sum_{\alpha\in A}x_\alpha=\sum_{\beta\in B}x_{\phi(\beta)}.$$
Note that when dealing with signed sums, the above rearrangement identity can fail when the series is not absolutely convergent (cf. the Riemann rearrangement theorem).
I think the above rearrangement identity always holds.
Example:
Let $A:=\{1,2,\dots\}.$
Let $x_\alpha:=(-1)^{\alpha-1}1/\alpha.$
$$\sum_{\alpha\in A}x_\alpha=\sum_{\beta\in B}x_{\phi(\beta)}=\infty.$$
Am I wrong?
Note that $$\{\sum_{\alpha\in F} x_\alpha:\text{ }F\text{ is a finite subset of }A\}=\{\sum_{\beta\in G} x_{\phi(\beta)}:\text{ }G\text{ is a finite subset of }B\}$$ holds.
And if $S=T$ holds, then $\sup S=\sup T$ holds.
You are wrong, sort of. It depends on what you meant and on what Tao meant. See this, as Tao says.
The essential problem is that a conditionally but not absolutely convergent series of reals will necessarily have that both its negative and positive terms diverge when taken as individual series. So you have a lot of money in the bank: you can keep adding negative terms to get to an arbitrary negative point, or keep adding positive terms to get to an arbitrary positive point. More precisely the Wikipedia page shows that for any extended real number $M$, you can reorder the terms of the series so that it converges to $M$. In this sense, reindexing with some $\phi$ miserably fails!
You took $1-1/2+1/3-1/4+\cdots$ as an example. In the sense of: $\sum_A=\sup_{F\subset A}\sum_F$ (which is actually a Lebesgue integral!!) you’re right that the sum of this series is $\infty$. This will always be true for a conditionally-but-not-absolutely convergent series by the Riemann series theorem. So in that sense I suppose Tao means that allowing negative terms means you get pathological behaviour. Series you think are convergent end up not being ‘integrable’. Moreover it’s usual to define a Lebesgue integral (series) in that way for positive functions (sequences) only and then extend it to generic functions (sequences) by taking the difference of the series of positive and negative terms. That would be undefined since we’d have an $\infty-\infty$ situation.
If you take a conventional series we have: $$\sum_{n\ge1}\frac{(-1)^{n-1}}{n}=\ln2$$
Consider $1-1+1/2-1/2+1/3-1/3+\cdots$ which, as written, converges to zero as a conventional series. Rearranging as follows: $1+(1/2-1)+1/3+(1/4-1/2)+1/5+(1/6-1/3)+\cdots$ yields $\ln2\neq0$. Whether or not rearrangement is well defined depends on whether or not you want this Lebesgue-style definition of series or the more conventional one (limit of partial sums).