The tragus is a thick area of cartilage, but (at least in my experience) not terribly painful to pierce. It seemed to take a long time because there's so much tissue for the needle to penetrate, but all I really felt was a lot of pressure.
Some people experience a loud popping sound in their ear when they get their tragus pierced. That doesn't mean there's any kind of damage to your hearing or anything like that - my theory is that this sound comes from the needle breaking the skin. Since it's so close to your ear drum, it's bound to sound very loud. If the needle isn't extremely sharp or if your tragus is extremely tough, you may hear that popping noise, but it's nothing to worry about.
Any ear cartilage piercing is tricky to heal, but the tragus especially gets in the way when talking on the phone, listening to earphones/earbuds, or using a bluetooth earpiece. It's best to avoid all of those on that particular ear for a few weeks if possible. Germs that are likely to be on those ear devices aren't conducive to healing, either.
Typical starter jewelry would be a 16 or 14 gauge CBR or micro curved barbell. Keep in mind that the ball end of a barbell tends to get in the way even more than a CBR when using ear devices. I learned that the hard way when I tried to listen to my mp3 player. I ended up switching back to a CBR.
Anti-Tragus - The prefix "anti-" is used with piercing to describe a pierce that is located across from the original piercing bearing its name. For example, the anti-tragus is opposite the tragus.
Expected healing time for a tragus or anti-tragus is anywhere from 3-6 months. A change of jewelry is usually ok after 6 weeks.