It will most likely take a long time until 1.9 will be released (considering how large the previous updates were, and how long it took to release them after the official announcements).
1.8 was released 236 days after its first snapshot.
But they have still shown the biggest features of the update via Twitter, so it can't be too long, especially since 1.8 was released quite a while ago.
The updates they have shown were pretty small (One new dungeon type, quivers, arrows, shields and stuff like that). They can either make a small update or a big one. If it's a small one, mostly dedicated to combat - Updating the server and its plugins will be done quicker.
New additions can only improve the server.
Yes, they changed (Removed blocking with swords) and might change a little more, but it won't affect the whole code (Unlike 1.8).
Adding on to what Mint said, sheild will be added and the ability to hold two teams in your hand. They might add a new ore. In my opinion Minecraft is becoming a mod.
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