Doesn't solve all of it, but that's why I use random localparts instead. Sometimes people wonder whether the address is correct, but if I confirm that it's ok that it looks weird, people aren't overly confused and just accept it. I then have it all integrated with Mutt so it tags emails with a human-readable label and automatically selects the correct source address when replying.

>But it does get awkward quite a few times when having to interact with a human (customer services, hotel bookings, etc) via email or phone when they get a bit confused why their company name is my email alias....

I had that problem so many times that I whipped up a quick Rails app that generates new email addresses. Type in the company name, hit submit. It uses a random project name generator gem to create something like SteelyFishSauce@<mydomain>.com, displays it on the screen, and emails "<Company name> has been associated with SteelyFishSauce@<mydomain>.com" to the spamcatcher address.

Same here, same (minor) problems. The human interaction part is pretty much covered when I used [email protected] for registration, but the more provocative variation [email protected] occasionally raises some eyebrows.

The nasty part is replying with the main address as the sender. I'd really love to have email clients with reasonable support for this usage pattern for the platforms I use, but maybe then the pattern might become popular enough to lose some of its advantages.