I've used a coworking space in Tokyo for approximately 2 years, including my entire tenure at Starfighter. It costs approximately $350 per month. A++ would use a coworking space again. I have visited the WeWork office that Erin and Thomas work out of in Chicago, and it is better equipped than my office and has a variety of features which make it better for doing the kind of work that I'm routinely doing, including a) vastly more space per person, so that other people's conversations don't intrude into focused productivity time and b) closed offices with decent acoustics for calls.
Previously I did substantially all of my work from either my apartment or from cafes. Offices are better than apartments: you can bracket all time spent in them as "work" and then go home from work. Offices are better than cafes: it is expected that you will be working at an office, and you don't have to play a constant am-I-paying-enough-to-keep-my-table game with the cafe. Relevantly for Tokyo cafes, offices (even cramped offices) are substantially more spacious per seat than cafes are, have much better power/Internet situations, and often include printers and fax machines, for when you need a printer and/or fax machine.
Working from home definitely has its own hardships. For me, its really messed with my sleep. When I worked from an office my most productive time was around 8am - 12pm. From home my post productive times are from 11pm - 3am. You can imagine some of the adverse effects this can have..
My first experience working in shared offices was at co-working spaces in Tokyo, Yokohama, Sendai, and Sapporo. I really liked working at coworking spaces in Japan. Once I came back to US, I tried several coworking spaces including WeWork. None came close to my experience in Japan. I rather work at home in US and at coworking spaces in Japan. Japan coworking spaces are very cost effective, flexible, facilities are top notch (specially internet speed), quiet, and you can be as social as you want or not. There are no gimmicks like beer on tap but some spaces held weekend/after-hour drinking and gaming (poker). I found US coworking spaces to be noisy and interrupting. Most have tenant agreements that run long (UW startup hall took the cake with 24+ pages) and basically ask you to sign your life away to them but they don't take any responsibility for anything.
Previously I did substantially all of my work from either my apartment or from cafes. Offices are better than apartments: you can bracket all time spent in them as "work" and then go home from work. Offices are better than cafes: it is expected that you will be working at an office, and you don't have to play a constant am-I-paying-enough-to-keep-my-table game with the cafe. Relevantly for Tokyo cafes, offices (even cramped offices) are substantially more spacious per seat than cafes are, have much better power/Internet situations, and often include printers and fax machines, for when you need a printer and/or fax machine.