Hi Julie,
I'm so glad that you're checking out all of the options for Disney's PhotoPass services. If you were to look through my family's vacation scrapbooks, you'll spot at least a dozen PhotoPass pictures in each one!
In all four Walt Disney World theme parks, the number of locations where you'll find PhotoPass photographers has dramatically increased over the years. However, I unfortunately don't recall seeing any PhotoPass photographers around Disney's Boardwalk. As for Downtown Disney, the only spot I know of that has PhotoPass photographers is the Bibbidi Bobbidi Boutique (inside the World of Disney store).
As for your second question, the
private portrait sessions are amazing. There is a separate fee, so I'd recommend calling the cast members at Disney Fine Art Photography & Video at (407) 934-4004 to get the latest info on packages and prices.
If you decide to schedule a private portrait session (which I highly recommend!), here are a few tips from your buddy Derek that will definitely help:
1) The photographers do an amazing job of selecting locations for your portraits. However, if you have a specific place (e.g. the beach at Disney's Polynesian Resort) or backdrop (e.g. a waterfall), feel free to let your photographer know.
2) Make sure you arrive a few minutes early for your session. These services are super popular, so they have to keep a very strict schedule. If you show up late, it's likely that they'll still have to end on time.
3) Opt for the earliest session available in the day. In the morning hours, there will be fewer guests trying to maneuver around you and your family while you're trying to hold still for the camera.
I hope that helps! Please feel free to write back if you should have any additional questions.
Best regards,
Derek