I am just starting to look into these.

I have come up with what I think will be a legal route and just wanted to run it by some of the experts.

I would like to make more mileage but my admit the gf will not be wanting to do a lot of that. But I always listen to ideas.

1: JFK-LAX: 1st of 1 (North America Transcon)
*1: JFK-LAX: 1st of 6 (North America)
2: LAX-LHR: intercontinental. Possible 1 day stop here
3: LHR-FCO: 1st of 4 (Europe) 5 day stop here traveling by train. Doesnt matter to airline as we will arrive and leave from Rome so no overland to them.
4: FCO-LHR: 2nd of 4 (Europe)
5: LHR-DXB: 3rd of 4 (Europe) stay here. also seperate ticket to maldives and back.
6: DXB-HKG: intercontinental. one night here
7: HKG-SYD: intercontinental. one night.
8: SYD-CHC: 1st of 4 (Southwest Pacific). near a week. same as rome.
9: CHC-SYD: 2nd of 4 (Southwest Pacific)
10: SYD-HNL: 1st of 1 (intercontinental entry to North America without immediate transit & departure). Spending a few days.
11: HNL-LAX: 2nd of 6 (North America)
12: LAX-ORD: 3rd of 6 (North America)
13: ORD-NYC: 4th of 6 (North America) Start of several month stopover.
14: NYC-MCO: 5th of 6 (North America). Later in year going to MCO on same ticket. Is this possible?
15: MCO-NYC: 6th of 6 (North America)

Specific question would be the 1 transcon limit. I assume that is only a limit on actual non stop transcons and not a limit on touching the coasts.

Also I am wondering how stopping in NYC will effect things as I would assume a stop over at home would not be allowed but dont know. I can sub in swf or hpn or can i force the issue that aa says ewr is no co-terminal with lga/jfk.