My daughter has done PL twice. She loved it. The first time she did it, the place was packed. While we didn't wait long to get started, we had quite the wait to get into the treasure room.
The second time was this past July, and her appointment was around 10 a.m. There was only one other child in there at the time. We had actually booked two appts (one for our four year old too- she refused to do Pirates League). One of the "Pirates" actually painted my four year old child's' nails for free since she didn't want to actually participate and the CM wasn't doing anything else. They didn't have the costume my daughter wanted in stock in her size so that was a bit of a bummer because I didn't bring a costume expecting to buy one. DD rolled with it. In the end, it was probably better because it was so hot in July. She was probably cooler in her shorts and t shirt.
Both times, there was no PhotoPass Photographer for us. I would definitely bring a camera. The first time there was a PP photographer outside PL who took my daughter's photo next to the PL sign after we finished the process. The second time, there was not a PP photographer in site anywhere around the area.
Makeup remover wipes are helpful. They do give you one in your treasure bag to take with you (you get quite a few things - my girl loved the treasure bag), but depending on who much make-up is applied it may not be sufficient. We didn't really have an issue with the makeup running either time. In fact, my DD went swimming the first time when she did the mermaid package, and it stayed on pretty well. In July, her she did the empress package, and there is minimal make-up with that package so while we didn't have an issue, I could see someone who does the package where their entire face is covered in make-up might have an issue.
I attached some photos, but I'm not sure how relevant it will be given you have a son who is likely to choose different packages.
