I love it. Recently been rewriting Goleko.com backend in Go from Python. The errors as value paradigm is so nice for 90% of the time. It is so much more robust code out of the bat.
I love Cadd and I have been using it for a few years now.
The documentation is kinda crap, but I still use less time to get things done.
Most projects are just copy/paste of old config files.
Everytime I had a problem, I asked and got an answer within 2 days. And nice answers, not like Stackoverflow...
I am not american so I might be a bit unenlightened here.
But it sounds weird that San Francisco is running so bad and their put their faith in a "hero" dressed as an Swedish furniture store.
I would say the same for almost any company, but I've been with Hetzner for like 7 years and the prices, support and up-time is unbeatable. They're this German company, and if anyone knows Germans there are very keen on security. I trust my ID there more than I do at any bank that have it.
It depends on what you want from it, but it sounds like you want an adventure.
If I were you in this case, I'd only plan to take cc + cash + passport and some clothes. Don't overthink it.
Try to go to a hostel and stay there with other people. Just follow whatever happens (without doing too much dodgy stuff).
Hostel people know how to have fun and find weird things to do.
Also, be prepared not to sleep and "relax" though, so maybe only do that for half of the vacation.