How to make modded, plugin server for MINECRAFT?

I couldn't quite find another similar question that fit exactly the way I liked so I figured I would just have to ask myself. We used to do vanilla, but have since gotten bored, so please don't bring up just doing vanilla unless you want me to lose it.
So my brother and I are looking to make our own personal modded/plugin server for a group of friends. The PC running the server is 64 bit windows 10, we have 32gb of ddr4 ram, and more than enough processing power for anything else needed, so for the most part that bit should all be taken care of.
The problem is, is that in past we have tried doing this and there are always some sort of errors and then of course the crashing starts. I wasn't the one doing it, my brother was, so now that I'm taking over I want to make sure I do it right and we don't end up putting tons of hours in just to lose data somehow.
What I'm wondering is how to make a server that allows both plugins and mods. What should I used? Bukkit, Spigot, Forge, cauldron, mod something api, anything else? What is and what isn't compatible on what I just listed? Does the version of which I use matter? Please give me your recommendations based off of what you would want a person who is just learning how to do servers, not simply based off of opinion.

Keep it simple and concise please, I get lost in all the advanced lingo and terms. Also if any of you know, could you tell me which of these would/wouldn't be compatible together as an extra? I figured these would have to be more trial and error for when I'm starting up. How would you do it if you wanted a child to understand basically lol.
ALSO we wanted to have like super legendary sacred mythical weapons that you have to work extremely hard to get and complete a ton of challenges, any ideas?

Addons: Admin, Voxelsniper, MCEdit, World Guard, Vault & bPermissions, clear lagg, group manager, essentials, world border, herobounty, MCMMO, Biomes of plenty, giant trees.

User Content: Multiverse Core & Portals, Citizens and Denizen, Lockkete Grapple hook mod, backpack mod, furniture mod, optifine, shaders, voxelmap, damage indicator, treecapitator, crafting guide.

So first, use Bukkit. It might be a bit hard to get, but try hard to get it.
After that it is pretty simple. On the minecraft wiki you can search "How to set up a bukkit sevrer" and it will give way better answers that Y/A
Then go to curse to get the mods for it, and put the mod JAR's in the mods folder.
Launch the server, then done.

AGAIN: MINECRAFT WIKI HAS A GREAT GUIDE

You have to pay for your own server, and I doubt you want to do that.