This is basically the GPL vs. BSD/MIT/Apache vs. Public Domain debate. I've been on all sides at various points, currently I'm on the side of the GPL for "big stuff I want total copyright over (requiring people to sign copyright waivers)" which lets me change the license later or give out proprietary licenses at a fee. For other stuff that may be useful to someone and that I don't care about, I like the MIT license or the Do-what-the-fuck-you-want-version-3 license. If I don't care, I'll either forget to mention or it will be public domain.

The problem with public domain is that outside of the US, in some countries "public domain" is actually more restrictive than e.g. the MIT license. So if you want to help users worldwide, you either need to research local laws or use a simple US-law-based license.

The benefit of the GPL, as I like to phrase it, is that it chains its users with freedom whether they like it or not. It's a very viral license and infects a lot that it touches. (Some businesses are even worried that the GPLv3 is vague enough that "distribution" could mean over the web, which would make the AGPLv3 redundant.) If you look at Stallman's free software song, particularly the part that goes "When we have enough free software/at our call, hackers, at our call/we'll kick out those dirty licenses/evermore, hackers, evermore", you can interpret that as saying once enough software respects user freedoms by default, then yes, we don't need the concept of licenses anymore to force it upon them. The GPL uses copyright as a weapon, as do the Copyleft folks, as do the MIT/etc license folks. As a side quip, this is also similar to basic Communist philosophy: you just need totalitarian control for a little while to set everything up, then the government can dissolve itself and everyone will continue working together.

The MIT/etc. license folks subscribe to the idea that the more things you can do, the more freedom you have. While this is true as a single developer, if you again take into account the end-user freedom then the utilitarian argument can go either way. A program licensed under the GPL makes sure all users of that program and its derivatives are free, regardless of its popularity. A program licensed under the MIT leaves the door open for someone to take that code and put it into another program that's licensed under something restrictive, and all of that program's users are not free. However, some programs don't become popular precisely because of the (A)GPL, whereas an MIT project that's used in a popular project (regardless of that derivative project being MIT) often becomes popular itself.

So for the GPL, the total freedom utility is just num_users for the program and all its derivatives. For MIT, if a non-free user is as bad as a free user is good, it's num_users_under_free_license - num_users_under_nonfree. You can see what needs to be satisfied to choose one over the other. There's also a factor involved for profit if you or someone else wants to make money on the software without the risk of legal source-or-binary redistributions.

I think Stallman recognizes the tradeoffs as well, I've read somewhere he doesn't like but accepts the idea of software (such as video games) initially launching as proprietary while it's in its peak profit window (first few weeks for games, traditionally, though that is changing with DLC), and then later relicensing as open source. Same thing with dual licensing.