We consider voting on multiple independent binary issues. In addition, a weighting vector for each voter defines how important they consider each issue. The most natural way to aggregate the votes into a single unified proposal is issue-wise majority (IWM): taking a majority opinion for each issue. However, in a scenario known as Ostrogorski's Paradox, an IWM proposal may not be a Condorcet winner, or it may even fail to garner majority support in a special case known as Anscombe's Paradox. We show that it is co-NP-hard to determine whether there exists a Condorcet-winning proposal even without weights. In contrast, we prove that the single-switch condition provides an Ostrogorski-free voting domain under identical weighting vectors. We show that verifying the condition can be achieved in linear time and no-instances admit short, efficiently computable proofs in the form of forbidden substructures. On the way, we give the simplest linear-time test for the voter/candidate-extremal-interval condition in approval voting and the simplest and most efficient algorithm for recognizing single-crossing preferences in ordinal voting. We then tackle Anscombe's Paradox. Under identical weight vectors, we can guarantee a majority-supported proposal agreeing with IWM on strictly more than half of the overall weight, while with two distinct weight vectors, such proposals can get arbitrarily far from IWM. The severity of such examples is controlled by the maximum average topic weight $\tilde{w}_{max}$: a simple bound derived from a partition-based approach is tight on a large portion of the range $\tilde{w}_{max} \in (0,1)$. Finally, we extend Wagner's rule to the weighted setting: an average majority across topics of at least $\frac{3}{4}$'s precludes Anscombe's paradox from occurring.