The last several months have been a great experience but also a major roller coaster. I moved out of my place in Chicago at the end of December, and was homeless for quite some time thereafter. Between the round the world trip (3 months), time in the US (~6 weeks of crashing on couches or with family), and some settling time in Tokyo* before I got a place (~6 weeks), it was a full 6 months until finally moving in to a new place at the end of June.
*I was staying in a hostel called Ace Inn, same place I had stayed on the January trip to Tokyo. It’s fine for a short stay, and stupid cheap, but not exactly an ideal long-term living situation:

The setup. It’s a capsule-style hotel. I paid up ($40/night vs $30) to get on the floor that had the desks. The lower floors were even more crammed than this. Advantage was that most of the time, people were going for the cheaper option so I generally had most of the floor to myself.

The bed. The mattress is like 3 inches thick. Ferociously uncomfortable. The bottom bunk opens the other direction so there’s another desk on the other side.
So, that was not awesome. Ideally I would have been out of there much more quickly. Of course, apartment hunting in a foreign country is also a bit of a challenge.
Aside from a 2-week trip to Singapore breaking up the process, it also took some time to get the lay of the land. The Japanese rental process is a bit different than in the US. There are generally not requirements for lease lengths, which is cool since I don’t really know how long I’m going to be here (more on that later). However, they get you hard in some other ways.
Basically, any time you want to start a lease for an apartment in Tokyo, there are 3 things you need to pay up front:
Agency fee: a commission for whatever real estate agency helped you find the place. Usually about 1 month’s rent.
Shiki-kin: this seems to basically be like the security deposit in the US, to be used as a reserve against the damage you and your crazy friends are going to cause. Generally another 1-2 months worth of rent, and it sounds like it’s a little harder to get it all back at the end. Who knows.
Reikin: this is the ridiculous one. It gets referred to as “key money” but literally translates as “gift money”. Apparently the idea of it is to give a gift to your landlord (another 1-2 months rent) to show your gratitude for allowing him to let you move in. Or something incredibly stupid like that.

Hey there! You seem like a cool guy. Have a stack of cash!
So, to summarize: if you get an apartment, you can stay as long as you want. But it might cost you a couple thousand bucks up front just to get in the door.
Conclusion:

I opted to go the share house route instead. Share houses are a setup where a bunch of people live in one house with shared common areas (kitchen, living room, etc). It’s kind of like a dorm but for big kids. They also have none of the up-front money other than a security deposit, and you can leave whenever you want with 30 days notice. Much nicer arrangement.
Share houses are pretty common in Tokyo as a way to cut down on the total living space needed. This is important.

Because it’s kinda crowded, yo
Quality of course varies dramatically based on the setup, other tenants, house rules, etc. After looking at a few places, I eventually snapped up one in the Akabanebashi neighborhood right at the base of Tokyo Tower (which was, until the opening of Tokyo Sky Tree a few years ago, the tallest building in Japan).
No, but like really, right at the base. It’s awesome.

The view out my window

View from the rooftop, in what undoubtedly ranks in the top 5 for most flattering pictures of me ever taken
To address a question up front: yes, this is basically an exact replica of the Eiffel Tower. But one caveat, and this is important: this one is 8m taller. BOOM, TAKE THAT FRANCE!

Note that originality in architecture is not valued highly around here.
And now, a barrage of random photos of the place:

Entrance of the building. Remodeling was just finished in June so everything is in fancy shiny new form, and all the residents are new as well.

Kitchen (photo credits go to my buddy JingJing, who seems to have decided not to send me any that he is also in. Now I just look like I’m vain and have paparazzi follow me literally everywhere. Thanks man.)

Ok, I lied. But he’s too shy to show his face. Anyway, here’s the rest of the roof view.

Room. It’s not huge, but it works. Size is about 8.5 square meters. Whatever that means. The metric system is kind of ruining me.

Common area TV room. Japanese TV is fantastic to watch with other foreigners. It usually involves a comically simple activity (example: a guy trying to pick a lock. We, no joke, actually saw a half-hour game show about this) with a bunch of commentators getting really, really into it. I have this vague suspicion that it would be much less entertaining if we actually understood the language.

Being an Asian house, we are required to take shoes off at the entry and store them in a cubby. This rule was stated very forcefully. Apparently in this time of year, the heat and humidity combine to make…some very smelly shoes.

The trash system is the most complicated thing I’ve ever seen. We have separate bins for regular trash, plastic bottles, other plastic, cans, and “unburnable garbage” (which I think means electronics or something). This is the sorting system city-wide, but it’s hard to realize because you never, ever, ever, and I mean ever, see garbage cans in public spaces.

Fancy high-tech laundry with no English. The first attempt to do laundry involved me and a European guy pressing a bunch of buttons with no success, and eventually giving up and waiting for a Japanese speaker to come home. It turns out to be pretty simple — there is no hot wash (cold only) and the machine auto-calculates the optimum duration, water level, etc, by doing initial measurements on the clothes. Spiffy.

We also have one of those mega-fancy Japanese toilets with way too many controls on them.
The aforementioned high-tech toilet comes with one particular feature that causes trouble at this time of year. Specifically, it has a heated seat. This is a common feature in Japanese toilets, and it’s remarkably luxurious when it’s freezing out in the middle of winter.
It is NOT so fun when it’s 90 degrees* and humid in the middle of summer, specifically because we can’t figure out how to turn it off. As it turns out, the damn thing gives off so much heat that it noticeably elevates the temperature of the whole room. It’s boiling hot in there.
So, just picture this. You go in, do your business, you’re there for like 5-10 minutes, and you come out… totally dripping in sweat. How awkward is that, man? It’s pretty seriously weird. This is where you just scram and get yourself to an air conditioned room before anyone looks at you too funny.
*Yeah, 90 degrees. Take your metric system and shove it.

We’ve got 20ish rooms in total, spread over 4 floors. All the common areas are on my floor, which is great for socializing and terrible for productivity. It’s about half Japanese and half foreign so far, though most people speak English. Since it’s a new building, we’re still filling up the rooms.

A few doors away. Not shabby. Generally speaking, this is a pretty nice part of town with a lot of foreign presence. For example, we are near a bunch of embassies, the closest one being…Afghanistan! I’ll have to go make some friends there.
So that’s home for a while.
And with that, a life update. After much discussion over the last couple months, the fine folks at Voyagin have decided to relocate the company to Singapore. It’s a great move for the business as the product rapidly expands across Asia. The English-speaking market, strong startup community, convenient travel hub, and pan-Asian press all combine to make this a great destination to grow from.
However, for me personally, the idea of hitting the road again after just getting settled again wasn’t ideal. There will be several months of travel before the Singapore move so it would basically have involved living out of a suitcase for almost all of 2013. So, ultimately, I’ve opted not to continue through the move and am now scoping out new jobs in either Tokyo or the US. Of course, I wish the best for the Voyagin team in the future!
Never a dull moment. I’ll update once I know what’s next!
P.S. since I know everyone is going to ask: rent is ¥76000 (~$760)/month, with another ¥12000 ($120) for utilities, internet, etc. Not having to deal with utility companies in a foreign language is another enormous plus.