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.
WhatsApp can only get you so far.
ps. don't get me wrong, I like the idea, but you are likely going to burn these people out with tons of logistic issues.
But still, it sounds like fun and does solve the problem of lack of friends and focus for permatravellers.
Might be easier to aim this at micropreneurs with runway as more of an alternative to the shared workspace/exotic workaway though....
I could be completely wrong, though. There isn't enough info on the website to make hard guesses.
I think having a group or network of similar minded people would greatly help.
I have actually thought about this a lot, what if there is a network of airbnbs/hostels around the world which a group of remote workers agree upon to be more concentrated? I think co-working spaces do much of it right now, but it can always be improved upon.
I do think that something like OP would be too formal, as it doesn't give you the flexibility to deviate, which is why I think a more liquid network of at the start just several locations would work.
Btw, I liked your approach above very much, if you have a majority of the group do that (allowing individuals to divert), this could totally work
You got a nice simple idea, created a quick gmail account, built a quick SquareSpace landing page with collection form and now you are on the front page of Hacker News collecting some good data.
This my friends is quick and dirty and it works, if you can hack this idea and get it onto the front page of NH in 30 minutes you will make this happen.
Anyways, the page seems like a marketing test anyway, just to see if there is any interest.
"REMOTEYEAR@GMAIL.COM"
Really? You have a domain name, couldn't set up "contact@remoteyear.com"?
Even though I'm sure nothing was meant by that, it makes the whole thing sound incredibly unprofessional and simply detracts from the offer.
https://www.squarespace.com/pricing/
Still, they could opt for Google's business email so they could use Gmail's backend with @remoteyear.com addresses.
I understand that it may sound very compelling to many and I absolutely don't want to advocate against their "product"; just think about what you want. "traveling without any of the risks" also takes away much of the fun, adventures and personal growth you'd experience on your individual, non risk-free journey.