No itinerary. It's gonna be free and easy and will decide while on the road. that's why am thinking of getting a SFO-SIN on SQ (redemption) for immigration purposes (having a return ticket). will be in the US for up to 90 days, and will either head to canada or south america. only 1st 2 stops are confirmed (NYC and Arlington).
i'll probably be buying alaska miles for the one way SG-x/TYO-NYC on JL (biz or 1st).
Then RTW award cannot work for you since I believe you will need to book all the flights in advance.
Technically, you do not need a return ticket, just proof of ticket that you will be exiting US. So you can find airlines offering $0 refund fee and just get the full fare ticket.
SQ award ticket still has refund fee, plus the currency exchange difference. UA can actually charge in SGD, so you can go that route, if they refund to you in SGD (I've had refunds come back in USD and SGD, while I paid in SGD, was lucky and earned little bit for the forex).

