Quick suggestion, currently play.date/account/sideload is hidden from anyone who has not registered a device to their account. It is a sane thing to hide the sideload tab from regular users awaiting arrival of their playdate devices (because they have nothing to sideload onto).
My request is this: show the sideload tab to all users who have registered a device OR a simulator. This way developers who do not have hardware can test and troubleshoot the sideloading process.
P.S. Since I have hardware I can't see if this has already been fixed or if you can access play.date/account/sideload it directly via url and the tab hiding is just cosmetic.