Every website you have ever looked at is set in one of about eight typefaces, and it has been that way for fifteen years. Not because of a technical limitation. The mechanism for using any font you like has been in the specification since 1998 and shipped in a browser shortly after.
It went nowhere because of licensing, and it is worth being precise about why.
A typeface is licensed for use, not sold outright. When a designer buys one for print, the resulting artwork contains shapes, not the font itself, so the file never leaves the studio. Putting a font on a web server inverts that completely. The file must be sent to every visitor, because their browser needs it to render the page, which means publishing means distributing.
From a foundry’s position that is not a licensing question with a difficult answer. It is asking a business to place its entire product on a public server and trust that nobody takes it.
So they declined, for a decade, and everyone worked around it. Text got rendered into images, which cannot be selected, searched, or read aloud. Then people used a Flash object to draw headings, which is an absurd thing to do and was still an improvement. Now there are scripts that redraw text with vector shapes at load time, which is cleverer and also absurd.
Every one of those is engineering effort spent on a commercial disagreement.
Two browsers now support the direct mechanism properly, which puts the question back where it belongs. The foundries have to decide whether a font on a web server is a sale or a giveaway, and I think the answer they reach will be neither, because the honest position is that it is a sale with leakage, like every other digital product.
Music took roughly eight years to arrive at that conclusion and the argument was identical at every stage. Files can be copied, therefore selling them is impossible, therefore we need a technical restriction, therefore the restriction annoys paying customers and does not stop anyone else.
My guess is somebody sets up as a middleman, hosting fonts and charging by page view, which lets a foundry pretend it has not simply put the file on the internet. That is a fiction, but it is a fiction everyone can sign, and those tend to be the ones that unblock a market.