The gondola should be completed soon so you can access it with a short walk to Art of Animation.
If upgrading to Table service, I would recommend making reservations exactly 180 days (at 4am Pacific time) from date of arrival. The good restaurants fill up fast like Be Our Guest. (BOG). BOG is now 2 credits for dinner but is still only 1 quick service credit for Lunch which imo is the best value for lunch at MK.
We went at the end of September both times and the weather was pretty good at that time. It was mostly sunny and hot but not unbearable. Only had 1 day of showers. We fortunately missed Hurricane Irma by about a week the first time but Disney did a great job of cleaning up the parks.
Another tip is to use Uber if planing to stay late at the parks for Fantasmic or Happily Ever after. The lines for the bus back to the hotel can be very long so it will be worth it to take Uber back to the hotel. If leaving from MK, Uber is not allowed to pickup at the bus loop. They have to wait at the TTC. To avoid that rush, take the Monorail to the Contemporary (its the next stop) and have Uber pick you up there. There were already cars waiting at the Contemporary lobby so our car was already available before we even arrived. It cost about $12+tip from MK back to Pop but its well worth it considering the wait could be 2-3 buses which can take another 30-45 minutes of waiting.
Also, make sure, you book those Fastpasses at the 60 day window. The quickest to go are usually Slinky Dog, Flight of Passage, Test Track, and Seven Dwarfs Mine Train. We were able to go on Slinky Dog and the kids loved it.