E-mail and the extensions and extras that make it go and make it nice /are/ duct-tape. I wouldn't advocate for /anyone/ running their own mailserver unless they're totally aware of what they're doing and on top of spam issues.
When considering if running your own mailserver is practical for you, consider the total cost of ownership; you'll most likely be paying for a dedicated server (or vps, VM, or whatever the cool kids are using these days) which will require staying on top of all the "normal" things; monitoring, backups (and you'll probably want to test them), updates, what blacklists to use, ensuring that /your/ server doesn't end up blacklisted, etc. Unless you've been a sysadmin before and know what this all entails, I wouldn't really recommend it. If you're not part of some bigger org (a hosting co or bigger company), it'll also be harder to get your one-off no-name server removed from blacklists, since this looks just like something Joe Linkfarm would do. I could show you this one really simple trick that a mother found to whiten your server reputation, but...
As far as creating a VM image that sets all this up for you, it's kinda the point that it doesn't exist; mailservers don't work well when run by people who don't really care about them. It's quite far away from a "set and forget" deal. This is why many hackers / sysadmins still use GMail; it's not the best at everything, but it's OK enough at most things that it's the least hassle to use.
That all said, I do agree that it'd be great to have a service which offers both more control for power users (I'd love a mailfilter-style config w/regex support for GMail), better privacy (easy PGP integration, etc), tag support, threading, and normal IMAP support, but I'm not quite holding my breath. This seems like a decent problem for some start-up to solve :) It's not a "sexy" problem, but it's a real one.