It's dangerous to go alone...
take this!In all seriousness, I was a pirate for almost a decade before I came to CCP.
When you actually pirate, and actively look for targets rather than sitting on a gate or station blowing up rookies, its a very rewarding form of gameplay and can lead to some awesome experiences.
There are only three pieces of advice I'd give starting out:
The first is universal to EVE - Don't fly what you can't afford to lose. Even if you're a 150 million skillpoint character, if you're trying it for the first time then take something cheap and disposable out until you find your feet. T1 cruisers and frigates are by far the most cost effective, as well as the more recently added new line of destroyers. Once you're comfortable, you can expand a little and try more expensive hardware.You'll die a lot initially until you find your feet and become familiar with all the horrible bait tactics that big meanies use to catch you while you're innocently trying to ply your trade, but you'll start to learn their ways and kill them in the middle of the face pretty fast.
The second is common sense - Choose your targets selectively. You're going to need to initially when you're flying something disposable. Whether you're going for the kill and loot approach or the ransom, you'll need to be able to hold your own. In any of the ships listed above you'll want to start off with softer targets until you get used to playing the aggressor. Once you're comfortable, take the proactive approach and go looking for a fight to cut your teeth.
Finally, stick to your word. You ransom someone and they pay up? It's good business practice to let them go. Word travels quickly in EVE, and if you start screwing people over you'll end up with people telling you where to shove your ransom offer.
Regardless of how you approach it, Piracy isn't for everyone. I ran a pirate corp for 7 years or so as a player before I came to CCP, and I've seen all kinds of results. People who couldn't handle PvP losses, people who had a crisis of conscience and refunded all the stuff they destroyed to their victims, people who just couldn't earn a living, and people who got bored with having to actually look for targets rather than just getting an overview full of them during a fleet fight.
It's kind of a niche style of gameplay, sometimes it works for people, sometimes it doesn't.
Hope this helps.
