Disclaimer: This is only a partial answer as I don't manage to rule out the case of measures with values in the surreal numbers (or the completion thereof).
Precise question:
The precise question (as per discussion in the comments): Does there exist a measure space $(\mu, \mathcal{A}, \mathbb{R})$, such that the corresponding Sigma-algebra $\mathcal{A}$ contains all countable, dense subsets of the real numbers and such that the measure satisfies the following two properties:
$1.)$ all infinite subsets have positive measure.
$2.)$ If $A,B\in \mathcal{A}$, $A\subset B$, and $B\setminus A$ is infinite, then $\mu(A)<\mu(B)$.
If needed, the OP would allow for measures with values in surreal numbers.
Proof of non-existence (real-valued measure):
This proof works for measures in nonnegative numbers.
Such a measure cannot exist (if it takes values in the extended real line). Consider the sets
$$S_x=x+\mathbb{Q}.$$
There exists an uncountable set $\Lambda\subseteq \mathbb{R}\setminus \mathbb{Q}$ such that $S_x\cap S_y=\emptyset$ for $x,y\in \Lambda$ and $x\neq y$.
By assumption, we have for $x\in \Lambda$ that
$$\mu(S_x)>0.$$
Thus, there exists $\varepsilon>0$ and a countably infinite subset $\Lambda_1$ such that for all $x\in \Lambda_1$ holds
$$\mu(S_x)>\varepsilon.$$
Now pick one element $x_0\in \Lambda_1$ and define the sets $$B=\bigcup_{x\in \Lambda_1} S_x, A=\bigcup_{x\in \Lambda\setminus \{x_0\}} S_x.$$
Both $A,B$ are countable, dense subsets of the reals and $\mu(A)=\infty=\mu(B)$ (as they are the disjoint union of infinitely many sets with measure $>\varepsilon$). However, $B\setminus A=S_{x_0}$ is infinite, thus, $\mu(A)$ would need to be strictly smaller than $\mu(B)$.
Added: It is not clear to me how to deal with measures with values in the surreal numbers (as I don't know anything about surreal numbers). It seems that they are not complete (Completion of surreal numbers), thus, one would probably need to complete them first. I would then try to show that for every $A\subset \mathbb{R}$ countable, dense, and contains an some singelton with infinite measure, we have
$$\mu(A)=\sum_{x\in A}\mu(\{x\})=\sup\{ \mu(\{ x\}) \ : \ x\in A\}.$$
Ond could hope to run a similar argument as for the real case. However, that would require somebody who is better versed in surreal numbers than me.