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.