Ok, Seoul is out since Tom's business trip got canceled. Instead, I'm planning a short trip for the three days (plus weekend so total 5 days) I have off at the end of June. Bonus- my brother will be here visiting. I've got it narrowed down to Okinawa and Taiwan. Here is the summary of my logic:
Taiwan
a) I haven't been out of the country besides home in over a year and am getting antsy.
b) I've never been there.
c) It's nearby, which means i) cheap and ii) fewer hours on plane (critical in consideration of brother)
d) It's China (don't tell them that) but I don't need a visa
e) exposes brother to different Asian country

Okinawa
a) nearby (wins over Singapore for flight time)
b) beach (I would like to get SCUBA certified before doing Australia for winter vacation)
c) I speak the language (for the most part)
d) its different than the rest of Japan (think Hawaii-Okinawa used to be a separate country from Japan)
e) exposes brother to more of Japan and less of international customs clearance

Other considerations:
I can get cheap "birthday" tickets to fly within Japan during July. There is a 3 day weekend here in July, so I could go to Okinawa with Tom then and do the SCUBA thing. Or, if I go to Okinawa in June I could go to Nagasaki or Hokkaido with the birthday ticket, but then I would miss out on getting out of the country. I'm leaning towards Taipei and Tom is leaning towards Okinawa (but he travels out of the country all the dang time!).

So... your vote is.... (here it actually really really counts!)