Hoping to leave in 5 days (!!!) on a oneworld explorer 5 continent pass. Is this route OK? - it's a bit of a cludge.

Newcastle (via London)
Montreal
Anchorage (via Chicago)
Chicago
Vancouver
(overland)
Cancun
Havana
Cancun
Quito (via Florida)
(overland)
Santiago
Auckland
Sydney
Ayers Rock
Sydney
Bangkok
Tokyo
Newcastle (via London)

Some questions:
1) Is there a maximum mileage (I can't find any official documentation on this)
2) Can I get to a South Pacific island at all? I see I can't get to Fiji but the I need somewhere that doesn't need pre-booking due to there only being 200 beds on the island etc.
3) It seems a hassle getting to Anchorage, having to go via Chicago both ways but I suppose there is no other way
4) Any way of getting to Seoul from Tokyo?
5) Travel agent said that most flights from Santiago - Aukland would be booked even for next year? Is that right?

Lots of questions I know but I'd appreciate any help.

(ignore dates)

4 JUL 03 Fly Newcastle GB to Montreal QU CA
=========== Multipart 2 Flight Segments
----------- Part 1: ------------------------------------
BA 1333 Dep NCL 2:00 PM Arr LHR 3:05 PM Dur: 1h:05m
DepTerm: Equip:320 ArrTerm:1
Meals:M

----------- Part 2: ------------------------------------
BA 95 Dep LHR 5:15 PM Arr YUL 7:20 PM Dur: 7h:05m
DepTerm:4 Equip:777 ArrTerm:
Meals:M

7 JUL 03 Fly Montreal QU CA to Anchorage AK US
=========== Multipart 2 Flight Segments
----------- Part 1: ------------------------------------
AA 1481 Dep YUL 11:30AM Arr ORD 12:48PM Dur: 2h:18m
DepTerm: Equip:100 ArrTerm:3
Meals:

----------- Part 2: ------------------------------------
AA 726 Dep ORD 3:11 PM Arr ANC 6:35 PM Dur: 6h:24m
DepTerm:3 Equip:757 ArrTerm:
Meals

20 JUL 03 Fly Chicago O'Hare IL US to Vancouver BC CA
AA 701 Dep ORD 10:58AM Arr YVR 1:16 PM Dur: 4h:18m
DepTerm:3 Equip:M80 ArrTerm:M
Meals:L

20 JUL 03 Fly Anchorage AK US to Chicago O'Hare IL US
AA 725 Dep ANC 8:15 PM Arr ORD 5:01 AM Dur: 5h:46m
DepTerm: Equip:757 ArrTerm:3
Meals:S

23 AUG 03 Fly Cancun MX to Havana CU
Lan Chil 587 Dep CUN 7:20 PM Arr HAV 9:30 PM Dur: 1h:10m
DepTerm: Equip:763 ArrTerm:
Meals:

30 AUG 03 Fly Havana CU to Cancun MX
Lan Chil 584 Dep HAV 5:35 PM Arr CUN 5:45 PM Dur: 1h:10m
DepTerm: Equip:763 ArrTerm:
Meals:

31 AUG 03 Fly Cancun MX to Quito Mariscal Sucr EC
=========== Multipart 2 Flight Segments
----------- Part 1: ------------------------------------
AA 2192 Dep CUN 2:58 PM Arr MIA 5:45 PM Dur: 1h:47m
DepTerm: Equip:738 ArrTerm:
Meals:

----------- Part 2: ------------------------------------
AA 931 Dep MIA 7:10 PM Arr UIO 10:10PM Dur: 4h:00m
DepTerm: Equip:757 ArrTerm:
Meals

7 JAN 04 Fly Santiago CL to Auckland NZ
Lan Chil 801 Dep SCL 11:15PM Arr AKL 4:25 AM Dur:13h:10m
DepTerm: Equip:343 ArrTerm:
Meals:

2 FEB 04 Fly Christchurch NZ to Sydney NS AU
Qantas 46 Dep CHC 3:50 PM Arr SYD 5:10 PM Dur: 3h:20m
DepTerm:M Equip:763 ArrTerm:1
Meals:M

5 FEB 04 Fly Sydney NS AU to Ayers Rock NT AU
Qantas 726 Dep SYD 9:15 AM Arr AYQ 11:05AM Dur: 3h:20m
DepTerm:3 Equip:73H ArrTerm:
Meals:R

6 FEB 04 Fly Ayers Rock NT AU to Sydney NS AU
Qantas 729 Dep AYQ 11:50AM Arr SYD 4:20 PM Dur: 3h:00m
DepTerm: Equip:73H ArrTerm:3
Meals:R

11 FEB 04 Fly Sydney NS AU to Bangkok TH
Qantas 1 Dep SYD 6:15 PM Arr BKK 11:15PM Dur: 9h:00m
DepTerm:1 Equip:744 ArrTerm:2
Meals:M

19 MAR 04 Fly Bangkok TH to Tokyo Narita JP
=========== Multipart 3 Flight Segments
----------- Part 1: ------------------------------------
AA 6096 Dep BKK 9:50 AM Arr HKG 1:45 PM Dur: 2h:55m
DepTerm:2 Equip:320 ArrTerm:
Meals:R
Operated by: CATHAY
----------- Part 2: ------------------------------------
AA 6105 Dep HKG 2:55 PM Arr KUL 6:35 PM Dur: 3h:40m
DepTerm: Equip:320 ArrTerm:
Meals
Operated by: CATHAY
----------- Part 3: ------------------------------------
AA 7208 Dep KUL 10:35PM Arr NRT 6:00 AM Dur: 6h:25m
DepTerm: Equip:M11 ArrTerm:2
Meals:S
Operated by: JAL


18 MAY 04 Fly Tokyo Metro JP to Newcastle GB
=========== Multipart 2 Flight Segments
----------- Part 1: ------------------------------------
BA 8 Dep NRT 1:05 PM Arr LHR 5:15 PM Dur:12h:10m
DepTerm:1 Equip:744 ArrTerm:1
Meals:M

----------- Part 2: ------------------------------------
BA 1336 Dep LHR 6:00 PM Arr NCL 7:05 PM Dur: 1h:05m
DepTerm:1 Equip:320 ArrTerm:
Meals:M