Whew, that's quite a project you're taking on! I look forward to seeing the result :) As to the questions...
. It starts in early September; looking back at the start of YAWYW, you're right about the spring-break setting, but I had forgotten that detail until now, and wrote as though the first chapters were in the back-to-school phase of fall... The general course of the story runs over about three months (to early/mid-December) and skips the remainder to the point where the Sun is changed back, in early March.
. This wasn't really established until late in the story (Weirdo kinda picked up on some hints and canonized it,) but yeah, it's basically set in Minnesota. I always wrote Lakeside as something of a cross between Duluth (where I live) and Moose Lake (my old hometown;) Weirdo just made it official.
. Greeman would be the person to say for sure on this, but Hawkins is kind of a "Man-in-Black/CIA spook" character; definitely not a Guy Fawkes look. There's something of a description here.
. Good question; I can't remember that ever being established. I'd think probably a white oak...?
. Varies depending on the type of changed; Jay the fox-girl reporter is around three or four feet tall, while Jeff and Belle are giant-sized and mere inches tall, respectively. But I think most changed are generally within 6" or so of human norms, unless otherwise noted.
. Only chompy knows for sure at present ;)
I can't wait to see what you come up with :)
