I've been doing this for 5 years and while I agree that leaks are rare, it has been only smooth sailing.

I use thunderbird with an addon that automatically sets the responding email address, and have a script called "email" that generates a random address (no prefix or anything) and puts it in my clipboard. If I want to k ow what I used an email for, I can find it in my password manager or by checking from where that address first got mail.

Signing things up in person, I just use human-randomly generated strings.

In short: I have none of the problems the author has...