I would never do this with people who couldn’t pass the bar of “pays venmo requests on time”. That said, I set up recurring paypal payments for each of them and it’s not a huge deal. Scheduling-wise we’d generally rather overlap with each other, but in reality it doesn’t happen often unless it’s intentional. We have four properties and maybe ~12-15 people total (some own all, some own one), so they’re usually just empty.

I’m curious how the financial aspect of splitting it all looks?
I think I’m a bit younger than you, but I sometimes have a hard time getting roommates/friends to pay my Venmo requests on time. I can only imagine what it would be like if we owned something as significant as a property together.

I’m also curious how you all are able to be in each place when you want to be? It makes me think somewhat of a timeshare, and I’ve heard those are never available at the peak times you want to be in a place.

Nonetheless, appreciate you sharing your excitement & congrats on finally finding the place in Tokyo you’ve been looking for!