Bukkit

Firstly, I just want to say these ideas could be configurable, so players who like the current system could keep that.

Anyway, my idea is: Players can set their post boxes (chests) which the post man can deliver to. Instead of teleporting around to the players, the endermen would go about 15 (configurable) blocks away from a postbox and walk up to it. If there is another postbox within 15 blocks of a player he needs to deliver to, he will walk to it, otherwise he'll walk away a little then teleport.
The system would be more realistic, and would mean players are much more guarenteed to get letters. You can easily send them to an offline or AFK player and they wont have to click the enderman when it appears. They could still get a message saying they have mail in their letterbox.

You could also have a more expensive letter which goes instantly as the current system.

Commands:
/courier - command help, maybe displaying the costs of each command too.
/courier postbox - Click the chest and it becomes your postbox (and locked to you, either default in this plugin or via LWC etc)
/post [name] - Begin writing a letter to the person. You'd enter a chat mode similar to in Bookworm, and each line would get a message with "X characters remaining" - if you go over it will simply add a second letter. (You could then have the "Message from: Flenix (1 of 3) line)
/courier [name] - Similar system to above, but the instant delivery one. You hire a courier to deliver it directly :)

I could go into loads more detail with post offices and stuff, but I wont unless you think it would be a possible idea.

Hi!

If I separate your idea into two, I think you'll be happy that they're (almost) on their way :)

1) Separate /post into two actions. /letter to write a letter (multi line possible) and /post to send a letter. You can store letters and pass them around using any number of means, and they're also public. When you've /post:ed them, they become locked (TBD) to the receiver and courier delivered.

http://dev.bukkit.org/server-mods/courier/forum/30212-courier-1-0-0-planned-roadmap/#p1

2) Mailboxes. I'm torn. There exists a MailBox plugin and while I haven't tested it it seems I would just duplicate most of what's already there. I'll look at it since it's been requested a few times, but it's not high priority atm.

http://dev.bukkit.org/server-mods/courier/tickets/14-mailbox-enhancement/

I'll keep your issue open for the moment but lower the priority with the above comments :)

@defxor: Go

Wait, by using the first idea (write the letter, then post seperately) - you could surely use that WITH the mailbox plugin to do the second for anyone who wants it.

I'd not heard of that plugin before, so I might get it anyway (sending items would be cool) if you decide not to add it (as you said you're torn)