Thank you everyone for your advice!

For Greece, I agree it doesn't really make sense to hit an island between Naxos and the mainland. I could definitely go back to Athens (we climbed Lycabettus hill once and the views were gorgeous) but dread going in and out of Athens from the ferry port and airport. I'd like to stay somewhere close without having to rent a car. Luckily I have 11 months to figure this out.

As for Paris, thank you for the Pia Pia recommendation! The reviews are very good, and I was able to book a family room for 4 with two connecting rooms for 757 euros (must cancel within 6 days of our stay). I am not terribly familiar with the 20th Arrondisment, but the reviewers say the hotel is right by the metro. I guess you won't get classic Paris architecture but you do get peace and quiet, which is not the worst things.

I just got my contract for L'Oree du Lac - need to send a deposit through wire transfer. What are people doing these days? Is Wise good? We are in the U.S., and our bank charges $50 for a wire.

I suppose I can refine over the next 11 months(!) but this is definitely a terrific start. Thanks Fodors.

"but dread going in and out of Athens from the ferry port and airport"
Bluestarferries from Naxos usually arrive at Gate E7, a few steps from Port Square Hotel, Metro station and railway station.
Book a hotel close to Syntagma metro station and you will be fine for the airport metro too.

Five days in Annecy is fine if you mix lake time with one or two day trips. Geneva is easy for your flight to Greece, and buses are simple. It can feel pricey in peak August, but supermarket breakfasts help balance it.

The WIse app is great and beats the heck out of the old way of doing things like going to a bank and it takes a huge amount of time because nobody knows how to do it.