If the two cups of coffee are for one person, I don’t think you want them at the same time, one might get cold.
I think you can start to heat again sometime during the drip phase. Start to enjoy your first cup while the 2nd cup is heating. Then the time between 2 cups being ready is shorter than option 1 and not at the same time as in option 2.
For ultimately path-dependent reasons. In my storage unit, I have a Chemex, burr grinder, and thermos, so when I want drip I tend to make a 'pot'.
I was nomadic for a couple of years, and brought along a hand grinder and a Hario V60 O1. Despite being "sedentary" for almost a year and a half, this is still how I make coffee: I've been reluctant to duplicate my entire kitchen, and never got around to shipping everything I own across the ocean.
Which turns out to be a good thing, since I'm heading back to the mainland. But yeah, definitely make individual cups of drip!
I think you can start to heat again sometime during the drip phase. Start to enjoy your first cup while the 2nd cup is heating. Then the time between 2 cups being ready is shorter than option 1 and not at the same time as in option 2.