To hear some modern reformsters talk, you would think that the major obstacles to a world of school choice and "education freedom" are the public school system and its supporters. But there are significant obstacles standing in the way of a happy world in which families can send students to the school of their choice, and those obstacles have nothing to do with the public school system at all.
1) Cost.
In Connecticut, the average private K-12 school tuition is $23,980; $33,610 for high school. And that's an average. Top private schools cost big bucks just for tuition, and that's before you get to all the other extra expenses. There are schools that have generous aid programs (Phillips Exeter Academy will give you a full ride if your family income is under $75K).
But the cost of many private schools is prohibitive. You can argue that, well, a top quality education costs a lot of money to provide, but please don't do that if you're also a person arguing that public schools already get way too much money.
The notion that a voucher with a few thousand dollars will somehow offset this issue is silly. It turns out that some small corners of the world have implemented real choice voucher programs, and they are expensive as hell. This is not a mystery; the amount of money that is barely (if that) adequate to fund one school system cannot be expected to fund multiple parallel systems.
2) Restrictive admissions.
We've seen it over and over and over. If you are atheist same-gender parents of a child with special needs, good luck finding a school of choice for your child.
This issue has only gotten worse as First Amendment separation of church and state has been eroded in favor of "I can't exercise my religion unless I'm able to discriminate freely against those with whom I disagree." Education savings account (super-vouchers) bills now routinely include a non-interference clause, promising that just because you accept voucher funds, that doesn't mean you have to abide by any of the rules that government must follow. Carson v. Makin on top of Espinoza make it clear that a religious school can discriminate against some families freely and with tax dollar backing. It is school's choice.
Discrimination on religious and ideological grounds is only the most obvious portion of this. Even in the charter sector, school operators put a variety of hurdles in the paths of families to help weed out the less desirable. An absence of support programs for students with special needs as well as push out programs keep away the students who are more expensive to educate. Cutting costs by not providing transportation or lunch also block access for some students.
Private and charter schools put hundreds of barriers at their doors, restricting just who can gets to have a choice.
3) Irrational marriage with free marketeering
One of the great unquestioned assumptions of the modern school choice movement is that school choice must somehow be welded to a free market approach. But there's no reason that choice has to employ free market mechanisms, which are themselves in conflict with the idea of choice.
The free market is about picking winners and losers. Every business plan covers the question of "which customers will we serve, and which will we pass on by." Free marketeers argue that the market produces a wide range of options so that everyone has a choice, but reality does not reflect that idea. Take cable television; after a brief initial flurry of wide variety and available options, the various channels have all converged on large sectors of the profitable middle.
The free market is not interested in outliers and customers who require special attention (unless they have special buckets of money). If the goal is to get a quality education to every child in the country, the free market is notably ill-equipped to do that.
Worshippers of the free market tend to put the desires and freedoms of operators ahead of the needs and rights of students themselves; this continues to make charters and private schools less appealing to a large portion of their potential customer base.
4) People don't want choice.
People don't want choices; they want what they want. I don't look across the room at my wife and think, "This is the most extraordinary, wonderful woman in the world, and I can't think of a better possible life partner, but I still wish I had choices." When a restaurant offers my favorite food, I'm not disappointed that the rest of the menu isn't appealing.
People call for choices only as a means to the end of getting what they want. Choice has no value to them in and of itself.
The market is never going to push for more choice; it's going to push for That Thing I Want. We can see that in the current culture war landscape. Choicers of the Moms for Liberty type are not calling for more choices in school libraries; they're calling for certain choices not to be available for anybody. Culture war choicers are very clear in advocating for certain choices in education to be available to nobody, and are also clear that certain choices (e.g. Christian prayer) should be the only choice some folks have. Parents opposed to trans students should have a choice; parents of a trans student should not have any choice. Despite the frequent use of words like choice and freedom, it's clear that choice is not really the objective at all.
These four factors represent some of the greatest obstacles to School Choice Utopia, and yet.
We do not hear choicers calling on private to lower costs and offer more scholarships. We do not hear choicers calling on private and charter schools to stop discrimination and adopt more inclusive policies. We do not hear choicers talking about how some of the goals of a choice system could be accomplished inside the public system. We do not hear choicers declaring that a true school choice system can only exist if choices are available for every single student. Nor do we ever hear choicers saying that to achieve this goal, the country must be prepared to increase its spending on education.
Instead we get a lot of rhetoric about how the public system and teachers and "entrenched special interests" are the big obstacle to school choice. It's as if some school choice advocates are more interested in what they can dismantle than in what they can build.