Should I host a Minecraft Server.

You don't need that much money for a server, what I use is $9.95 for 1 month, which supports about 20 people. If you want extra performance space, it will cost $19.95, which if you had that many people on the server, then everyone would only need to donate like $1 or so.

You could start out hosting it on one computer and use all of that computer's RAM to run it, and see how that goes. If people like it and maybe start donating, then maybe you upgrade to Tree Puncher or something. People will like it a lot more if the server is different than all of the others (PVP servers are somewhat hard to find). And if it starts getting good, you can give people huge reward for donating, like moderator powers (if you trust them enough).

Don't use home server hosting, unless you have a powerful computer and a good network.

I can tell you a good host.