Quoting Ben Hutchings <b...@decadent.org.uk>:
Also, dedicated tiny flash partitions for the kernel and initrd. I wouldn't be surprised to be find that by the time we want to release buster we can't build a useful kernel that fits into the 2 MB partition that most of these devices seem to have.
Non-HF devices can be very different, look at e.g. this ARM926EJ-S one: http://www.taskit.de/stamp9g20.html
As it is, stretch will be supported until 2020, maybe 2022 on armel. Is it really worthwhile to add another 2 years to that?
This depends on the effort, of course. But for environmental reasons I'ld say the longer the better.