In all the years of developing for the Apple Watch, the process of trying to run my app on a physical watch or simulator through Xcode is still an absolute nightmare. I probably waste hours each day trying to get my app running. Either the watch doesn't show as paired in Xcode, or it's stuck setting the watch up for development, or it says it's running but Xcode just hangs, or it just doesn't show up in Xcode at all. I have to do so many combinations of restarting my watch, my iPhone, my Mac to try and get it working again. Sometimes it works, sometimes it doesn't and I just give up for the day.
Once I get it running I may have 5 times the app will start properly before going back to not running. When trying to use the simulator the watch keeps coming unpaired with the iPhone and won't run. And it's not possible to use Xcode with an iPhone that has multiple Apple Watches paired to it, which is annoying because I can't have one dedicated watch for testing. I just don't understand after all these years Apple Watch development just keeps getting worse and worse. I'm almost ready to just drop my Watch app completely, it's just not worth the headache we go through trying to develop it.