1. StompyNZ's API mod for servers allows POI's to be manually spawned in, other similar programs allow the same I believe, maybe check out his mod in General Mods and ask in his thread if you have any issues or need help.
2. Yes it is possible, I know GuppyCur did it on his server for us during experimental. May just be a case of copying the player data to the new game folder or similar.
Best I can do in answering these, I don't manage a server so can't personally assist sorry.