Ok so here I go again (get a snack because it's long), with some changing days around and what not, here are the final plans (assuming I can get ADR times similar to what I want)
All times are what I am hoping for, I can't make ADRs until June 20th and we'll be upgrading to AP so we'll have many days in WDW.
Some more prologue:
We're staying at Pop Century Sept 18-Oct 2 on free dining.
I have a surprise 3 night stay for me and my mom at WL from September 22-25 (she'd never spend the money on a deluxe so I will for her) we will have free dining here also but I have upgraded it to the DxDP.
We're staying the night of the Expedition Everest Challenge (Sept 26) at AKL for quick and easy transportation and we got a good rate for the night.
September 17
Flight, yuck!
Red-eye arriving at MCO at 6:04AM on Sept 18 with layover in LAX (I wish I had time to hit up
Disneyland)
September 18
Arrive 6:04AM
Hopefully to Pop by 7:30AM, we will check in on our 10 day mark hoping our room will be ready.
Option 1: If our room is ready, sleep until 11AM or Noon then go to Captain Cook's in the Poly for lunch, MK by 3PM.
Option 2: If our room isn't ready, go to Epcot until it is ready. If we have time, nap until 6PM where we will head to MK by then.
MNSSHP
Late dinner at Casey's Corner eat just before Hallowishes.
September 19
HS for AM EMH.
Head to Epcot as early as we feel like it.
Back to resort for a little rest.
DTD and
Raglan Road 8PM
September 20
AK All Day
Hopefully this will be the day we get to eat the picnic in the park.
The Wave 5:30PM
Either MK for PM EMH or back to resort for early turn in
September 21
Pick up rental car at Disney Car Center at 6AM
Outlet Store day!
Boston Market for lunch which my mom loves and we don't have anymore in Oregon.
Logan's Roadhouse for dinner which I love and we have never had in Oregon.
Grocery store and Old Town if we have the time.
Return car at 8PM
September 22
WL check-in
Crystal Palace at 11:30AM
MK day or lounging around WL
California Grill 7:30PM for 9:30 Hallowishes
September 23- Mom's Birthday
Kona Cafe 7:30AM
MK Day
Citricos 5:30PM
September 24
Food & Wine Festival soft opening
Epcot Day
Sunshine Seasons for breakfast
Whispering Canyon Cafe 8:30PM
September 25
Chef Mickey's 7AM
WL Check-out

Epcot All Day
First day Food & Wine Festival
Flying Fish Cafe 7:30PM
September 26
Possibly HS EMH AM
AKL check-in
Packet Pick-up for Expedition Everest Challenge
Sanaa 3PM
Expedition Everest Challenge 6:30ish
EEC After Party 8:30-Midnight
September 27
AKL Check-out
Donald's Safari Breakfast 8:05AM
AK All Day
Yak & Yeti 4PM
September 28
HS All Day
HDDR 7:15PM
September 29
CRT 8:05AM
MK All Day
'Ohana 7:45PM
September 30
Epcot All Day
Rose & Crown 12PM
Maybe DTD at night
October 1
Our last full day

MK All Day
Narcoossee's 6PM
Maybe DTD at Night
October 2
We go home, worst day
Last minute park going, I suspect either MK because we love it or HS because we don't have a lot of time planned here.
Flight leaves at 5:15PM