Several of the examples don’t seem to support the Up+Down reset to bootloader. Are they just too simple? Should I add a call manually during loop()?
It’s part of the Arduboy2 library, older examples using Arduboy library won’t support it, it’s depreciated but not really in any documented or practical way. Sorry about the tribal knowledge! Still working on getting a new developer guide up and running.
for example, in Arduino IDE, File > Examples > Arduboy2 > HelloWorld doesn’t seem to support it. Would it work if a .hex were a part of an uploaded cart?
IIRC in order to get that Up+Down reset to the bootloader you have to use @Mr.Blinky’s homemade package instead of the standard Arduboy2 library.
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It’s not.
Correct!
The feature is part of the Arduboy optimized core that is included with the Homemade package.
Probably yes. The cart builder tools will (try to) patch a hex will with this feature.
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As always y’all are right there with the answers, I’ll try this out!
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Ok, so apparently I learned you need to use the homemade package 
Because of this thread I added answers to the help and information category, it’s probably been a long time coming but too useful in this situation and others.