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

One problem I see is the KUL to NRT - you can't fly on JAL metal on a OWE - it has to be OW metal, which would eman CX via HKG, but that puts you over the 20 segment limit.

SInce you only have 4 hours in KUL I guess you don't have to do anything there as such, so just BKK-HKG-NRT on CX would do the job.

1) No
2) Yes - IPC and PPT (requiring using someone else to get from PPT to SWP). Lord Howe Island has been recommended by others (QF from SYD).
3) Also from DFW and STL and occasional flights which stop there but have a single flight number from somewhere else (e.g. CUN). But only June to September)
4) The shortest way is via TPE on CX. Requires two segments.
5) Perhaps true according to other discussions here.

NRT->TPE->ICN route is the shortest, however, you can not make sameday connection.

CX451 NRT-TPE 1615 1850
CX420 TPE-ICN 1710 2040

NRT->HKG->ICN is OK.