i dont think that anything you have suggested is unrealistic or naive in fact i have been discussing this with Skymanjay, nothing official, but we are thinking along the same lines for alot of it.

with regards to taking items over to the new the world, i am all for it,yes I have accrued a 200 something strong chest room, all full, but im not gonna cry about losing it all, rather than everyone being able to take all of their stuff, we should all be able to take over a double chest full of items each, easy to verify that you have it and not time consuming to sort out on the other side.
like you said, me or tom can easily confirm what you have in said chest, even a room could be made for each player to deposit their items to take to the new world easily and safely enough.

with regards to island sizes etc, we need to find a good seed for our map, lots of medium sized islands surrounding a few continents would be ideal
obviously, people teaming up to make their own villages would be nice, claim blocks can be used much more efficiently to claim islands tbh, and we do need to go over GP plugin configs to make sure they are safe, but still raidable if you leave the spaces for it to be possible.

the ships plugin to me isnt a big thing, its cool, but it needs to be regulated, raft size ships for new players and as you earn claim blocks you should be able to trade thiem for ship blocks or something, not sure if it could be implemented but would mean the longer you play the bigger you can build ships.

we need a big brain storm, get everyones wants on paper, andf find out a plan for the new world, no reason why we cant open a new world soon, and get it ready for players once the rest of the updates are stable?

These things sound very good!
If they can be turned into reality the server will become much better

Giving the (larger) islands a name probably makes the world less scattered as well, I guess.
It would make it more attractive (for me at least) to team up with other players and perhaps create factions or something like that, instead of the 3-man thief alliances that currently seem to be popular.

First step is back to square one, sort out the lag so were smooth, then we can discuss other things, I can easily transfur builds from server to server useing worldedit and I can make backups locally from a home hosted dev server which I could let people join to help me find things to move over, so thats a solution.
I need to make a decision, Do I stay with this current host and take their offer to moving to some EU servers (IP reset) and start a fresh world with the basic plugins we need, or Test out another server host with a fresh world, either will be a new world, with the plans we are on I doubt I would be able to run two worlds at once (old and new), unless I can find a way to do it smoothly.

As for the seed, thats the hard bit, It took me ages to find out current sea based seed, I havent even played any 1.7, but I know the terrain is completly different, Seas much smaller, I found one that might be good, two big continents seperated by a big sea with loads of little islands in there, but disgussing seeds is hard, because once someone knows the seed then can generate that map locally and run any software they want to find and exploit the map which would ruin gameplay.

I want users to build our landmarks, in legit. We have some fantastic builders.
EU is only responce time, Im giving our host this once last chance with Eu hosting and a fresh world to see how that goes, if its useless, we will change, but I will have to figure out a date to get a ton of users to max out the server when we are setup to test it and the plugins all together.
Game?
Either way we are getting ANOTHER IP change, I hate this, I really hate it. This is why I setup mc.piratemc.com, But that seems to be a few bars down.
No shit you guys that have stuck with me will be getting you’re own special perks/ranks, for this awful shitstorm (sorry).
I love the idea of owning land and battleing it out Crazy, but the legistics of it are hard! We have griefprevention, which overites any resedents/factions plugin.

When im setting up/deploying new tech, what would would be the quickest way of testing this with people? teamspeak/skype/google hangouts/fb/irc/add a web instant chat/etc ?

well, during weekdays would be difficult for me, and probably others too, but evenings, weekends, etc, I can make. And godsdead, we stuck with you to see this through, and so the server improves, you’ve been delt a bad hand, we just want to help, don’t need ranks to be a good person! Youre right, creating out own builds is cool, and adds charecteristics to the server. Still though, if man’o’wars, frigats,brigs and stuff where just world edited in, with cargo for pirates to steal, along with the ship. So each landmass has some ships, which players can loot and steal from. And the continates trade with eachother, so pirates blow stuff up on trade roots. And cool, a new map=AWESOME!