When "less restrictive means" are more restrictive of other interests

I'm writing an article on the use of "necessary," in the sense of "least restrictive means," in various legal rules - basically, rules that some action is allowed only if it's "necessary" to achieve some end, with necessary being understood as "there are no other comparatively effective ways of achieving this end" (or, this is the least restrictive means of effectively achieving this end). I plan to discuss this in various contexts, including (A) the law of self-defense and the duty to retreat, (B) least restrictive means tests in constitutional law, (C) the necessity defense in criminal law, and likely in some other contexts as well.

I was hoping I could ask people for a bit of help related to this, specifically on item (B). I'm looking for cases in which

1. a court (whether the Supreme Court or some other court) analyzes whether a law is necessary to serve a sufficient government interest / is the least restrictive means of serving this interest,
2. there are some alternatives that would serve the interest pretty much as well, but
3. those alternatives would burden some other important interests, whether governmental or private.

For instance, in 44 Liquormart, Inc. v. Rhode Island, the plurality and the concurrence struck down a ban on alcohol price advertising partly because there were less speech-restrictive means of serving the interest in reducing alcohol abuse - such as taxes, minimum prices, or limiting the amount of alcohol anyone could buy in a particular time period. But these alternatives would protect speech only at the cost of interfering with consumers' liberty, equality, or privacy interests. Taxes and minimum prices would burden the poor much more than the rich. Purchase caps would interfere with people's freedom to buy however much they want to buy, as well as their privacy, since the government would have to track each consumer's purchases.

I have a few other such examples in mind, but I'd love to hear more. I'm not saying that the 44 Liquormart result is wrong because of this, and perhaps even the logic is right, if we think the burdens on free speech rights are categorically worse than the burdens on those other interests. I just want to explore this line of analysis.

I could use both cases in which the court concluded that the law was unconstitutional because there are less restrictive alternatives, and ones in which it upheld the law because of the burdens those alternatives would pose. And I could certainly use lower court cases as well as U.S. Supreme Court cases. If you have some examples, I'd be grateful if you could pass them along!