Applaud your post
In vBulletin user banning options insert every email address and phrase that you can think of that might cause you being flagged as spam to the ban list, spam, postmaster, microsoft etc etc (because if a mod upsets a prick then a prick will sign up with the following to just be a prick)
I suggest assigning different email functions to different IP addressed and email addresses
newsletter=IP 1 : forum confirmation=IP 2 and so on, Now if you get marked as spam it shouldn't affect all your emails sent.
Now just pray that someone (that same prick) doesn't sign up using a honeypot address because most of the time these do not bounce and will result in your IP being flagged as spam.
If this happens then you will need even more IP addresses to do split email send outs to try and Isolate the bad email address. (start with the latest sign ups)
Before doing any mass sending I suggest sending a trial to
spamcheck@sitesell.net making sure that in the subject line you put "TEST". The email will bounce straight back and give you a spam score. (if you don't put TEST in the subject and in capital letters your email will just be dropped from the server instead of bouncing back with the results)