Everythings’s bigger in the U.S. than over here in EU, from parking lots to SD cards to presidential wisdom, isn’t it? 
You can go with any size of 4G or larger. Just make it two devices.
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It was the Russians fault.
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Did I learn my lesson about backups? Yes 
I make a backup copy of my entire configuration after any modification I make. But, openhabian has made it so simple to commission a brand new RPI that I don’t make any more image backups or anything of the sort.
Did I incorporate any of the other common sense/logic in your post into my life? No - sometimes, anectodal evidence and personal experience trump logic and common sense 
I have 5+ years of combined runtime on two of these USB sticks that outlived the ~1 month each of runtime on these SD cards, and if anything, my openHAB has gotten more write-happy with the increased number of devices/items/persisted states. I still use the same brand SD card as a boot device with the USB stick as the rootfs, so I think i’m beyond the scope of statistical anomaly and in the realm of probable root cause (SD card as rootfs = fail). Unless, of course, the two SD cards I had fail were B-stock duds, or came from a bad batch, but still - what am I doing different that keeps my USB sticks alive for such a long time?
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