I wouldn't say that English has 'many' homophones. And yes, I think they're generally very annoying, when they can be used as the same part of speech. There isn't much confusion between 'led' (past tense of 'to lead') and 'lead' (the heavy metal). However, it always takes a moment to catch up when someone uses 'right' as a verb, and I imagine 'righter' would be even worse, especially as an obscure jargon term.
We are getting a bit off-topic, so this is my last post in this thread.
I'd argue that this constitutes many (note the restrictions too, which result in excluded entries).
With regard to how noticeable homophones are, it feels to me like there is a priming effect due to the context, which results in the sense that was intended being obvious and coming to mind effortlessly. For example, cents and sense sound the same in some dialects, but I doubt many would even consider interpreting the sound in question as cents if they heard the previous sentence spoken. I...
To break up the awkward silence at the start of a recent Overcoming Bias meetup, I asked everyone present to tell their rationalist origin story - a key event or fact that played a role in their first beginning to aspire to rationality. This worked surprisingly well (and I would recommend it for future meetups).
I think I've already told enough of my own origin story on Overcoming Bias: how I was digging in my parents' yard as a kid and found a tarnished silver amulet inscribed with Bayes's Theorem, and how I wore it to bed that night and dreamed of a woman in white, holding an ancient leather-bound book called Judgment Under Uncertainty: Heuristics and Biases (eds. D. Kahneman, P. Slovic, and A. Tversky, 1982)... but there's no need to go into that again.
So, seriously... how did you originally go down that road?
Added: For some odd reason, many of the commenters here seem to have had a single experience in common - namely, at some point, encountering Overcoming Bias... But I'm especially interested in what it takes to get the transition started - crossing the first divide. This would be very valuable knowledge if it can be generalized. If that did happen at OB, please try to specify what was the crucial "Aha!" insight (down to the specific post if possible).