Since I did much of my planning based on this wonderful forum, I just wanted to return the favor. We recently left Amsterdam after a 3-day visit. FWIW, I have a few suggestions:
Canal tour: We booked a "luxury canal tour" through Airbnb experiences, with Matthew. It was not inexpensive, but my daughter and I both felt it was well worth it. Matthew has a small boat (fits 20 maybe?), and for this reason, he is able to take you on canals which larger boats can't explore. He begins by sharing some information about the history of medieval Amsterdam as you pass some early architecture, and as the tour progresses, he takes you right up to the present. Professionally he has been involved some canal feasibility studies for the city, so he knows a lot about the historical and as well as the present day use, construction, and infrastructure of the canals/canal system. He is wealth of information. He also offers you wine or soft drinks on the boat, and he is happy to just allow you to sit back and enjoy the ride, or answer any questions at any point. He is very laid back, but don't let that fool you, he knows quite a bit. We took a 4:30 tour which was perfect. At the end of the tour, he also told me stay behind and he gave me some personal suggestions of places to visit. He was right on in his suggestions!
Jewish Amsterdam Tour: After much debate, we went with Naomi Kooperman. Wow! She was phenomenal. Best guide ever. She spoke nearly nonstop for a good 3.5 hours. I'm usually that annoying person in the group who asks 1,000 questions. Well, let me tell you -- I barely opened my mouth. Naomi is a wealth of knowledge. She knows her history and you have a sense that she could share even more, given the time. She also knows all the people who work at the sites you visit, and twice, when we arrived at sites a little late (through no fault of hers), the people who work at the sites allowed us to come in, even though they were supposed to be closing! I would take any tour Naomi offers! In fact, we wanted to change our plans and sign up for a tour with her the second day we were there, but she was only offering the same tour again.
Anne Frank House: A must. While I have always found the diary and story moving, seeing the photographs of little Anne, and her diary written in her original handwriting, and really physically experiencing just how small the rooms she was hidden in are, was especially moving. Be forewarned, it is very very crowded experience. But they do a very nice job (IMO) of pacing/moving people through the historical setting. I was worried that we didn't have tix to the introductory program, but I don't think it made one bit of difference.
We also hit up the Rijksmuseum and the flower auction (need to take a bus for 45 min) - not to be confused with the flower market - and you should really be there by 7am. Both where also great!
Hope this helps,