Pretty interesting. This is what I've been doing for the last 12 months throughout Europe, but with a new location every 1-2 months.

At first the organisational details were the frustrating part, but after almost 12 months and 8 cities the lack of longer term friendships is more of a problem.

In regards to "the headaches of looking after 100 people", surely that's something that can be addressed by limiting the scope of services provided? I think handling 1) accommodation and 2) work would be more than sufficient for most responsible people.