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I had a classmate or two that moonlighted and we looked into it while I was a resident. The biggest issue for us was malpractice insurance since ours wouldn't cover us for moonlighting. The licensing was also an issue since we didn't all have full licenses, some just educational-limited licenses. Another issue was about billing. The way we had envisioned it was that we would take turns on a weekend going to some nursing homes and trimming nails with an attending. In order to bill under the attendings name, the attending needs to be there as well, and there weren't any attendings interested in giving up more than 1 Saturday a month. That boils down to just a few Saturdays per year per resident, which didn't even cover the cost of malpractice or getting a full license. Some of the residents I have heard of moonlighting did so by billing under the attendings name while the attending wasn't there, which we weren't going to do.
As has been mentioned, there are other specialties that are much more friendly towards moonlighting. The EM residents at my hospital could make more than their resident salary in moonlighting towards the end of their residency if they really wanted to. Their schedule (working ~15-18 shifts a month) makes moonlighting easier to happen. There were also opportunities for the IM/FM residents to cover shifts in the ICU and occasionally for surgical subspecialties to cover the trauma call if all the GS residents were at a conference. We couldn't cover trauma because we didn't have ATLS and couldn't cover ICU because we didn't do an ICU rotation. We basically were the poorest residents at my hospital.
As has been mentioned, there are other specialties that are much more friendly towards moonlighting. The EM residents at my hospital could make more than their resident salary in moonlighting towards the end of their residency if they really wanted to. Their schedule (working ~15-18 shifts a month) makes moonlighting easier to happen. There were also opportunities for the IM/FM residents to cover shifts in the ICU and occasionally for surgical subspecialties to cover the trauma call if all the GS residents were at a conference. We couldn't cover trauma because we didn't have ATLS and couldn't cover ICU because we didn't do an ICU rotation. We basically were the poorest residents at my hospital.