Unless you're going into the easiest residency of all time, I wouldn't recommend moonlighting until 3rd or 4th year.
This is how it worked while I was a resident, things could've changed.
1) You had to inform the program. The hours spent moonlighting counts towards your 80 hour maximum work limit/week.
2) You had to have a medical license to practice in the state. The rules here will vary per state. I have seen some states have differing requirements for foreign grads vs. AMGs. E.g. AMGs could moonlight after two years of residency training vs 3 years for IMGs. Remember, this was only where I did residency. It might not apply in your specific state.
3) You had to make sure your work was covered for malpractice by the institution.
And just to let you know, if I were a PD, I would not let anyone moonlight if they showed poor work. 1) A resident doing poor work IMHO has their priorities off if they want to moonlight but can't show me they can do good work 2) If they spend even more hours working elsewhere, that's less time and attention on the work they do in the program 3) No way would I allow a resident in my program who does crappy work be allowed to show his face and do crappy work elsewhere until he fixes his act.
PGY Is also don't have much of a clue of what they're doing. PGY IIs have a clue but it's a sophomoric clue. Yeah, they gave med x 10 times and it worked so now they think they mastered it. No way. It's not until you've given it 50 times and seen 5 guys get really bad side effects (the first time they get the side effects you freak out because you've never dealt with this before) with the med that you're on some level of competency with the treatments. This type of experience usually doesn't happen until the end of PGY II. You have to have some bad experiences with the treatments while under supervision (so the attending can save you and the patient) before you're ready to practice on your own.
If I saw a PGY I trying to moonlight, I'd seriously consider there are issues going on that need to be examined, e.g. this person may be a bit cocky to want to practice without really knowing how to do it well, the person's desire for money may be to the point where it brings practice under question, the person doesn't really know what they're getting into....