Having a second helps with justifying the hotel costs, sure, but they were nothing compared with the airfare, in this case. ($1500 for LA->Singapore->Tokyo->LA)
There's a kind of cast member pantomime that I learned when I worked at Disney World and would try to get visitors from other countries to go where I needed them to be. In Japan, I just tried to plug into the other end of that, to communicate whatever I needed as a guest (which wasn't much - again, I know my way around a Disney theme park).
For the most part, though, you just go where the arms point, while smiling and nodding in return. When you want to order food, just point at what you want. At buffeterias and table service locations, that's easy enough. At counter service locations, a cast member would come through the line handing small paper menus to each person. I'd just select what I wanted on that menu (which was written in both Japanese and English) and point it out to the person taking the order. (While saying "Arigato," when they rung it up correctly.) This practice is all sorts of awesome and I wish Disney would do this during the high season at Walt Disney World, too.
So even though I met only two cast members who spoke English to me while I was there, I didn't have any problem communicating (with one exception that I'll get to during Tokyo DisneySea week, and that one totally was my fault).
As far as accommodations, I stayed at the Hilton, which has enough bilingual staff to address any issue you might have. And English is the international language of aviation, so there were no problems whatsoever at the airport.
The biggest problem I faced was making Priority Seating reservations at Tokyo Disney. You can do this online, but only via the Japanese version of the Tokyo Disney website. This was the one place where I cheated, and pulled a string I had inside the Disney company to make my reservations for me.
Of course, there is a Disney park in Hong Kong now, with another under construction in Shanghai. But I find it interesting that more Asians from outside Japan don't go to the Tokyo Disney parks.
To lessen the hassle, read up on literature. You don't want to waste time once you arrive.