Disclaimer: Though this thread is written in a Q&A style any new thoughts are really welcome!
What reasons are there to restrict measures to countable additivity rather than uncountable additivity? Is there a deeper reason than just it "works"? Any scratchy ideas are welcome...
Mainly, sets and numbers rely on different footings.
That brings structural similarities but also structural discrepancies.
These allow one to study homomorphism as are measures only to a certain extend.
To start with, both give rise to an algebraic structure by a binary operation admitting a neutral element: $$A\cup\varnothing=A=\varnothing\cup A$$ $$x+0=x=0+x$$
Now, these extend to finite operations due to associativity: $$A_1\cup\ldots\cup A_N$$ $$x_1+\ldots+x_N$$ (Also noting that commutativity holds for both!)
At this point finite additivity can be studied...
Next, the union immediately generalizes after a reformulation: $$A_1\cup\ldots\cup A_N=\{x\in X:x\in A_1\vee\ldots\vee x\in A_N\}=\{x\in X:\exists i\in\{1,\ldots,N\}:x\in A_i\}$$ arriving at the union over arbitrary collections: $$\bigcup_{i\in I}A_i:=\{x\in X:\exists i\in I:x\in A_i\}$$ The sum however requires the introduction of a Hausdorff topology.
After this first lack arriving at the sum over in principal arbitrary collections as well: $$\sum_{i\in I}x_i:=\lim_{J\subset I:\#J<\infty}\sum_{j\in J}x_{j}\quad J\leq J':\Leftrightarrow J\subseteq J'$$ (Note that both extensions are independent of reordering by construction!)
The main two differences however are that not every arbitrary collection of numbers has a convergent sum and if so then only countably many numbers can be nontrivial: $$\sum_{i\in I}x_i\text{ exists}\implies x_i\neq 0\text{ countably many}$$ The first point forces positive measures to lie within the extended positive real axis and complex measures within a bounded disk: $$\mu(A)\in\overline{\mathbb{R}}_+\text{ resp. }\mu(A)\in\mathbb{D}\subseteq\mathbb{C}$$ The second point is that tells us* (but doesn't force us**) to better consider merely countable collections.
*A bad situation usually mentioned: $\sum_{x\in[0,1]}\lambda(\{x\})=0\neq 1=\lambda(\bigcup_{x\in[0,1]}\{x\})$
**In fact, the Dirac measure possesses the uncountable additivity!
So sigma additivity will be the most prominent candidate for structure preserving homomorphisms a.k.a. measures.