I played regularly for years. Then I joined the army and it didn't seem like a lot of fun in retrospect. When I got out, I once again enjoyed the sport but as a poor college student I didn't really want to spend my money on such things. Thus, I switched to the more wallet friendly fencing, which surprisingly enough is actually quite similar.
With regards to the pain aspect, I'd have to assert that there are only four places that really hurt to get shot. In order from least painful to most we have:
Groin - Shots to the groin generally bounce which is a plus. The pain lingers longer than in most places but one can continue playing without much trouble.
Pinkie - Of all the fingers, the pinkie is the most painful. It doesn't linger as long as the groin at least but it is far more intense.
Spine - More painful still than the pinkie, a shot in the spine is more than enough to stop whatever you're doing at the moment. It is also nearly guarnteed that said shot will break.
Base of the Sternum - At this particular location people are unfortante enough to have a nerve cluster very near the skin. A shot in this location actually causes blinding pain (similar to a broken bone, though it does not linger nearly as long) and makes it difficult to breath for a few moments. I have only been hit in this location a few times but each time I could do little more than lie on the ground for a few moments and struggle to breathe again.
I will say that there are a surpring number of ways to play. From simple walk on recrational games that have no objective save eliminate the rest of the opposing team to tournament play or even scenario games where hundreds or thousands of players all partake in an objective based game. For any paintball players who are looking for something to do in Early June and are located close enough to eastern Oklahoma AND have a few hundred bucks to spend, I'd suggest the D-Day Oklahoma big game. I went once and there were nearly 2,000 players, armor, artillery and air support. It was staggeringly expensive (I was just out of highschool and waiting to leave for the army so I still had my crummy high-school job) given that the event (a total of about 30 hours on the field for me) consumed 4 cases of paintballs (~8,000). At 120 USD per case, plus the entry fee and lodging, it was the most expensive endeavor I had undertaken at that point. There are other big games and scenario games. If you live in the North East US, you're pretty much in the heart of paintball country and could reasonably play in an event or two every month of the year.