So....what Disney planning thoughts are floating around in my head that I can update you with? It seems like so many things are "to be determined".
Update on earning the PChef trip
As of now, Judy should have met all the requirements to earn the trip.

This year (and maybe last year, I forget) consultants have to reach a certain number of points (you get points for sales, recruiting, promoting, etc.)
and have a certain number of recruits. She is actually over in points, but needed one more recruit (who had to meet minimum sales to count as "qualified"). So, we're good to go there.
We're watching the progress of a couple of ladies under Judy in the hierarchy. One, is in a similar situation as Judy was, so we'll have to see. She has five kids, so assuming she earns it, that's the family we'll probably be splitting an extra hotel room with. The other, appears to be too far away points-wise to make it. It's actually very sad because they've got a couple of boys who are the perfect age to go and I was so looking forward to seeing them experience WDW for the first time. She had more than enough recruits, but is short in points, and there's just not enough time left in the year. That's one problem with these incentive trips, if you don't make it it can be very de-motivating.
When to arrive?
The DVC portion of the trip is booked, set in stone. And the PChef portion has specific days too, but they begin on a Sunday. We still have Annual Passes from last year's trip that'll be good for while we're there, so why not show up on Saturday? Wait, hold the phone! I saw that there's a 5K run at the Animal Kingdom on that Saturday, I'd love to do that....so, fly in on Friday? Um, Friday is the last day of school. And there are no "snow days" built into the calendar, so the last day of school could actually be
during the PChef portion of the trip. It better not be!
Arriving on Saturday looks like the most likely scenario right now, while crossing our fingers for no snow days, or forgiveness to miss the last day of school if it gets extended. But even that could add another hotel room change to our already split-stay trip.
Tickets
I
think this is one area I've got figured out. Now, you astute readers I'm sure noticed that I mentioned above that we have Annual Passes, but in my introductory post said that we'd be upgrading tickets.

Well, as part of the trip package we'll receive 3-day tickets, but I doubt that they're non-expiring, PChef probably wouldn't pay for that when they're intended to be used right then. So, my plan is to use our Annual Passes while we're there, but upgrade the tickets we get from PChef to add the non-expiration option, and to add some days for use next time.
Park Plan
I wanted to include some park plan info. in this post, but I'm not where I can access it at the moment, so it'll have to wait. But, I can tell you that by looking at the park hours that were recently issued, I got it down to a choice of two parks for each day. But I have no idea how much touring Judy will want to do with her consultant friends, so the whole thing could be up in the air. Not a good thing, for a planner like me. Times a'wastin'!!
ADRs
This is the scariest. Actually, our ADR window for the PChef portion of the trip opens today, but we don't have reservations made yet because PChef won't do that until the incentive earning period closes. But it doesn't matter anyway, because I don't have the park plan done. Our ADR window for the Kidani portion of the trip opens Friday, but again, I don't have a plan! I think I want to do Hoop de doo for our last night, to go out with something special, but other than that, I don't know yet.
Well there you have it -- a look inside my brain, and the amorphous mass of unknowns and issues it contains.
Link to next chapter