Should I play this server?

[Supaskillz]

Yes.
Just be aware classic Everquest is brutal in many ways. Dying comes with a real cost: you will lose xp and have to go get your corpse from where you died. I think this aspect is great as you feel accomplished when you evade death. Also Traveling requires actual journey. Only wizards and Druids are able to port to a variety of locations ( although at lvl 29 onward they can take others with them).

Guilds take a range of sizes and goals. You can read about sone of them in guild discussion forum here, but in wouldn't worry about this right off. Try to group and make friends and decide about a guild later.

Take a look at p99 wiki. Ask questions in starting zone forum. People are knowledgable and helpful here.