The problem here is that there isn't really any concept of an "uncountable sum" for you to have an intuition about! Summation is initially defined as a binary operation, then extended to finite sums by induction, and then extended to countable sums by taking limits. That is as far as it goes. The closest analogy we have to a "sum" over an uncountable set is the integral. We can make some valid probability statements involving the integral that are similar to the quoted claim, and involve integration as a kind of "uncountable sum". Below I will show what you can and can't validly say.
What we can say
Using integration as our version of the "uncountable sum", there is a rough analogy that holds here in probability theory that mimics the intuitive properties put forward in the quote section. Suppose we have a continuous random variable $X$ with quantile function $Q_X$ and density function $f_X$. Then the norming property of probability gives:
$$\int \limits_\mathbb{R} f_X(x) \ dx = 1.$$
For any $x \in \mathbb{R}$ we have $\mathbb{P}(X=x) = \int_x^x f_X(x) \ dx = 0$ and yet we can get any quantile value $0 \leqslant p \leqslant 1$ by taking:
$$\int \limits_{-\infty}^{Q_X(p)} f_X(x) \ dx = p.$$
This means that the "uncountable sum" (actually an integral) over a bunch of outcomes with zero probability can give us any probability value we want between zero and one. This occurs because our "sum" is really an integral that is "summing" an infinite number of infinitesimally small values. That is essentially what this kind of "intuitive" description is pointing to.
What we can't say
Unfortunately, it is not possible to extend this idea to get an exact analogy to the quoted section. Even taking the integral as our concept for an "uncountable sum", an exact analogy to the quoted section would be something like the following invalid result:
$$\ \ \int \limits_{-\infty}^{Q_X(p)} \mathbb{P}(X=x) \ dx = p.
\quad \quad \quad \text{(Invalid equation)}$$
The reason this does not work is that $\mathbb{P}(X=x) = \int_x^x f_X(r) \ dr \neq f_X(x)$. When we extend from the countable domain to the uncountable domain, and start dealing with "uncountable sums" as integrals, we start using infinitesimals. These infinitesimals are small enough that they give zero probability when we integrate over a single value, but they are actually larger than zero, so when we integrate over a larger (uncountable) set of them, they can give a positive value.
Consequently, we can see that the result really comes down to the fact that, once we start using an "uncountable sum" we also need to start using infinitesimals, which are infinitesimally small non-zero values. If we were to translate the quote into a strictly valid observation on mathematics, it would say that even though infinitesimal values look like zero from one perspective (e.g., integrating them over a single value), an integral of infinitesimal values can be any non-zero value.