I've used both the one world validator and mileage monkey and they both say this trip is ok, but I went down to the Cathay office today and after 2 hours of teeth gnashing they told me this wasn't a valid itinerary. Here's the routing:

ICN-HKG-DPS-HKG-LAX-LAS-JFK-STT-JFK-MAD-BCN overland to VCE-HEL-LED-HEL-ICN
(on mileage monkey btw it denies there is service between Las Vegas and JFK, AA has a direct flight at like 07:30 every day, but I then outed it through DFW on mileage monkey and the itinerary still came up ok)

They gave me a long litany of problems that weren't problems(claiming some of the flights didn't exist, like the HEL-ICN route that begins June 1, or that St Thomas isn't in North America so it would be 4 continents) but finally we seemed to get by all that. But in the end, they said I couldn't do it because I am over the limit in Europe. Is that right? I guess the question comes to does the overland Barcelona to Venice segment count as one of the 4 European segments or does it just count against the 20 total, but the 4 European continent count.

I can probably just get away with cutting Madrid out of the picture(since I was really going to spend a little more than a week training over to Portugal and around, I can just do it from Barcelona, adding 3.5 hours each way to my round trip on the train), but was more than a little frustrated by the airlines lack of knowledge of their own affiliates flights and rules.

No. MAD-BCN//VCE-HEL-LED-HEL counts as five segments for the total of 20, but it is only four flight segments. The continental limit of 4 is for flight segments, therefore that part of the trip is definitely valid.

Viajero is correct (of course!) and in fact in the technical rule sheet on oneworld.com, they highlight this:

Thanks, they were so insistent(basically half an hour or so of arguing this) that I started to wonder if I was misunderstanding things.

Just one small thing Deslok - since you're starting in Asia, you're only allowed two stopovers there; so one of your visits to HKG will need to be a transit - either on the way to DPS or on the way to JFK.

Also, I presume you're purchasing a xONE3, not a xGLOBx - there are different rules for the GLOB ticket

Yeah, actually both my transits of Hong Kong are under 24 hours, would have gone straight to Bali if I could, but have to route through Hong Kong to get there, and to get over to the States(although that was one of the other issues Cathay was trying to give me, that I couldn't "stop" in Hong Kong, New York, and Helsinki twice, even though one of each is a transit under 24 hours).

The people in your local Cathay office obviously do no know the details of the xONEx ticket - there is NO restriction on multiple stopovers at the same place. You are allowed to stopover twice at JFK and HEL; the only reason you cannot at HGK is because of the 'two stopovers in continent of origin rule' (and even then you could have both of the allowed stopovers in the same place if you wanted to!)

I suggest you go back to them armed with a printed copy of the technical rule sheet

The problem is that I'm also in Korea(hence the ICN start and end of the journey) and the additional language issues that result. At one point, the woman tried to pull out what is presumedly the Korean version of that sheet to point to a line claiming it said what she claimed. Having only the most rudimentary Korean knowledge, all I could say was that in English, here's what the rules from the web site say. And we could go to the site and double check(or hey, even use the validator on one world's actual website). But all that would have made too much sense for them. I think I'm going to try a travel agency next, that I think may have some more familiarity with the RTW ticket rules and who can take whatever time it takes to get this done, because I refuse to sit for another 2 or more hours in their office arguing back and forth. Crossing fingers that it works.

Since you'll be flying AA for some of the sectors - have you considered booking through the AA RTW Desk? There are plenty of posts in this forum reporting good experiences doing this - just search for 'RTW desk'

The TA is probably going to charge you a service fee. If they do there is another 'fee' option you might want to consider instead, one often used with clueless, recalcitrant ticket offices: planned reissue. The idea is to have the OWE issued as a bare bones electronic ticket, one that will not challenge the inept local office too much, with the idea of reissuing it later at a planned, savvy location. It costs money, but it could save your hair.

LAS-JFK added to MM now, thanks.

Please post things like this in the MM discussion thread, I don't normally notice them in other threads. Thanks Mwenenzi for the tip here

I may give that a shot(if I remember to pickup a calling card sometime tomorrow for calls back to the states... or borrow a friends skype).