The biggest annoyance I run into is e-mail address fields that refuse to accept addresses containing subdomains on the right-hand side of the address. My provider allows me to create on the fly addresses in the form of "firstname.lastname@example.org" which come in handy when I suspect the recipient of that address might re-sell it. When I fill out a form (like for Sears, for one example) that refuses such addresses, it makes me not want to do business with such people, as it clear that they hire RFC-illiterates to design their IT systems.
I suggest plus (or dot) mail addressing instead, which is at least a standard:
Those will all go to
email@example.com in GMail at least.
I used plussed addresses before my provider offered the subdomain option, and switched to the subdomain option because many web forms reject the plus sign as an invalid character. More RFC ignorance.
I know about the Gmail dot thing; it doesn't allow me to customize addresses as flexibly.
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