Here's an alternative formulation that proves that it can't be done with three (non-adaptive) guesses:
Let $U=\{A,B,C,D,E\}$ be the 'universe' here, with the subset we're guessing at then being $S\subseteq U$. Label our three guesses as $T_0$, $T_1$, and $T_2$ (and note that this formulation assumes that we've made these choices beforehand; i.e., that $T_1$ is chosen without any knowledge of the value of $\left|T_0\cap S\right|$). For each of the five elements $e\in U=\{A,B,C,D,E\}$ associate a 3-bit 'inclusion code' $I_e$ that says which of our three subsets of $U$ the element is in: for instance, if our guesses are $T_0=\{A,B,C,D\}$, $T_1=\{B,C\}$ and $T_2=\{C,D\}$ then the inclusion codes are $I_A=\langle1,0,0\rangle$ (since $A\in T_0$, $A\not\in T_1$, and $A\not\in T_2$), $I_B=\langle1,1,0\rangle$, $I_C=\langle1,1,1\rangle$, $I_D=\langle1,0,1\rangle$, and $I_E=\langle0,0,0\rangle$. We'll call the number of 1s in an inclusion code its weight; in this example, the weight of $I_A$ is 1, the weight of $I_C$ is 3, etc. (Note that for our guesses to have any chance of succeeding then every $I_e$ must have positive weight; otherwise we'll never be able to detect the presence/absence of $e$. This leaves seven possible values of $I_e$, from which we'll be choosing five.)
Then the 'winning condition' that we can successfully determine any subset of $U$ based on our guesses is exactly the condition that the 32 vector sums $\displaystyle\{\sum_{e\in E}I_e : E\subseteq U\}$ are distinct (since if any two of them are the same, then the corresponding subsets of $U$ are indistinguishable).
Now, we can knock off the rest with some case-based analysis using the pigeonhole principle. First, as noted above, we trivially can't have any of the $I_e=\langle0,0,0\rangle$. Now, suppose we had e.g. $I_A=\langle1,1,1\rangle$. Then we have four other $I_e$ to distribute amongst the weight-1 and weight-2 slots. But any way you distribute those four, one of the weight-1 inclusion codes will be complementary to one of the weight-2 inclusion codes, and so they'll sum to $\langle 1,1,1\rangle$. This means that there's no solution with a weight-3 inclusion code, and so the five inclusion codes must be distributed among the six possibilities of weight 1 or 2; but however this is done, either all the weight-one slots will be used (in which case some pair of them will add to one of the used weight-two slots) or all the weight-two slots will be used (in which case the pair of weight-one slots that are used will add to one of them).
There may be a more direct way to show this based on linear algebra; another formulation of the 'all sums distinct' condition is that there's no linear combination $\sum_{e\in U}a_eI_e=\langle 0,0,0\rangle$ with the coefficients $a_e\in\{-1,0,1\}$. Now, since we have five distinct vectors in $\mathbb{N}^3$ they're clearly linearly dependent, but it's not immediately clear to me that the usual proofs for linear dependence (e.g., Gram-Schmidt orthogonalization) won't lead to coefficients larger than 1. If that hole can be patched, though, it's obviously a much cleaner proof.