Well, the server move is now done, and it's been a day or so. As such, I'm willing to call that success.
So, the first thing to comment on. Money. I stated that I do not intend to ask for donations to this server. That is still true. If you guys must know, it costs me $24 a month to run this server. I am more than happy to run it so long as you guys are still logging on and enjoying it. And honestly, I'd feel terrible about taking some college kid's money. I was in college many years ago myself, I get what it's like.
So, looking ahead, we have 1.14 coming out soon. As of right now, my plan is to upgrade the server when the first somewhat stable spigot release comes out. These sorts of upgrades are tricky, as it's usually a question of which plugin is going to break, and here's hoping it's one that is still supported so it will be updated. Usually it takes about 2 weeks after the official Minecraft release to get Spigot, then another two weeks to get things to a state where I'm happy to upgrade the server.
That being said, I haven't really done this since the 1.8 -> 1.9 update, so here's hoping they've done some streamlining. But as things happen I will definitely keep you aware.
But that brings me to my ultimate point. When 1.14 comes out, what do you want to do? My first instinct is to keep building on this world. But if everyone wants to, we can definitely restart the map, or even select a different map. I'd love to hear what you guys thing in the website forums!