It has been tried multiple times, particularly in print media. Most people, regardless of what they claim, aren't willing to pay for ad free. Just the pure fact that it used to be free, often makes it even harder to convert them.
You say you're willing to pay for ad-free, but I'd ask why you aren't paying for ad free already. Many websites now offer it, and few pay it (e.g. almost all online news, Reddit, Google's ad network, YouTube, etc.
It has been tried multiple times, particularly in print media. Most people, regardless of what they claim, aren't willing to pay for ad free. Just the pure fact that it used to be free, often makes it even harder to convert them.
You say you're willing to pay for ad-free, but I'd ask why you aren't paying for ad free already. Many websites now offer it, and few pay it (e.g. almost all online news, Reddit, Google's ad network, YouTube, etc.