As others have said, we, hopefully, will update to 1.9, but it will take time to see how things play out with the new update. It may have a cruddy launch, like Halo MCC did, so they want to guarantee that it will work properly.
Plugins will be easily updated as there aren't many internal changes in fact the server software J&H use is already testing snapshot versions. The only thing holding them back is the people who hate nearly every update because it will "ruin" something (*cough*pvp*cough*). So I would say not as long as 1.8 but still substantial.
Agreed. Of course THAT literally can't happen until 1.9 actually comes out. My guess is three to four months after the initial release of 1.9.