Looking for help figuring out some minecraft server admin stuff

[rapn3rd]

I'm trying to set up a minecraft server that is semi-vanillia. Pvp, some land protection using Grief Prevention, essentials, other drops and a few other plugins and it's looking like essentials stops being supported on 1.8 and beyond. I'm using bukkit but is spigot better? I haven't been playing mc for about a year and the last time I set up a server was also about a year ago on 1.7. Is essentials, and the mods I want to use a complicated endeavor on 1.8 onward?  Any advice or tips would be welcome, I'm running into a lot of problems with essentials that I think might be a result of running on 1.10.2, instead of an earlier version.