This is not a complete answer, but is too long for a comment.
Consider the following generalization of your problem: (Maximum Weight Halfplane) We are given a set $S$ of $m$ weighted points in the plane, and a special point $p\in S$. Find a line such that the sum of the weights lying on the same side as $p$ is maximized.
Recall also the (integer) 3SUM problem: Given an array $A$ of $m$ distinct integers, does there exist three distinct elements $a,b,c \in A$ such that $a+b+c=0$?
Claim: If we can solve the Maximum Weight Halfplane problem in time $O(m^{2-\alpha})$ for some $0<\alpha<1$, then we can solve 3SUM in time $O(m^{2-\alpha})$.
Sketch of a reduction:
Start with an instance $A$ of 3SUM. Let $\epsilon = 1/5$. For $0\leq i\leq m-1$, define $p_i = (A[i], A[i]^3)$, $p^+_i = (A[i], A[i]^3+\epsilon)$, $p^-_i = (A[i], A[i]^3+\epsilon)$. Let the weights be $w(p_i^+)= 1$ and $w(p_i^-)= -1$.
Define an additional point $p=(0, \infty)$, with weight $w(p) = 10m$.
Consider the instance of Maximum Weight Halfplane $S=\{p\}\cup(\bigcup_{0\leq i\leq m-1}\{p_i^+,p_i^-\})$, where the special point is $p$.
Note that the maximum weight halfplane necessarily contains $p$. Moreover, if the maximum weight is at least $10m+3$, this means there are at least three distinct indices $i_1,i_2,i_3$, such that the separating line passes between $p_{i_1}^-$ and $p_{i_1}^+$, between $p_{i_2}^-$ and $p_{i_2}^+$, and between $p_{i_3}^-$ and $p_{i_3}^+$. Thus, the line passes through three points $(A[i_1], A[i_1]^3+\delta_{i_1})$, $(A[i_2], A[i_2]^3+\delta_{i_2})$ and $(A[i_3], A[i_3]^3+\delta_{i_3})$, where $=-\epsilon \leq \delta_{i_1},\delta_{i_2},\delta_{i_2} \leq \epsilon$. Some algebraic manipulation shows that this is equivalent to
$$(A[i_2]-A[i_1])(A[i_1]+A[i_2]+A[i_3]) = \frac{\delta_{i_3}-\delta_{i_1}}{A[i_3]-A[i_1]} - \frac{\delta_{i_2}-\delta_{i_1}}{A[i_2]-A[i_1]}.$$
Assuming $A[i_1]+A[i_2]+A[i_3] \neq 0$, and because these are all distinct integers, the left hand side in absolute value would be at least $1$, but the right hand side in absolute value is at most $4\epsilon < 1$, which is a contradiction. Thus $A[i_1]+A[i_2]+A[i_3] = 0$.
The same kind of reasoning works the other way around: if there are three indices such that $A[i_1]+A[i_2]+A[i_3] = 0$, then you can find a hyperplane of weight at least $10m+3$ containing $p$.
Thus, if the 3-SUM conjecture is true, then you can't solve Maximum Weight Halfplane in strongly subquadratic time. In your problem you have $m=n^2$, so this would give an $\tilde{\Omega}(n^4)$ lower bound (if the reduction worked for points on an $n\times n$ grid, which unfortunately it doesn't).