Pros
If you're looking for a summer job and have a group of friends you want to work with, then give College Pro Painters a try. Work in crews of 3-5 people and paint houses while getting to be out in the sun and talking with friends. The pay is decent, around minimum wage of $10-11 per hour in Connecticut.
Cons
Depending on who your boss/manager is, your training will vary. If you're lucky you will spend your first week with an experienced crew on a house with a flat landscape that will allow for easy and steady ladder placement. If you're not so lucky you may be stuck with a house on a hill where ladder placement feels impossible and you'll be spending your first day on the job 20+ feet in the air clinging to the ladder while attempting to paint a house for the first time.