I'm guessing it's an older OE install that was cross-graded to LE at some point. OE used a 235MB boot partition and LE 7.x/8.x are around 230MB so fit within that partition size constraint. The LE 9.0 image has grown a little due to drivers and such and the 235MB boot partition is now too small to host the files so the upgrade aborts. To fix this you have two choices:
a) Backup the LE 8.2.5 install and move the backup file off-box, then clean install LE 8.2.5 (which gives you a 512MB boot partition) and then restore the backup; then update to LE9.0. This is normally the fastest option as most LE installs only have 1-4GB of actual Kodi data on the /storage partition that needs to be backed-up and moved and the reinstall/restore process is quick.
b) Boot an Ubuntu (or similar) LiveUSB and use gparted to shrink and then relocate the /storage partition to create space for the boot partition to be size expanded to 512MB or 1GB (whatever you fancy). This is normally the slower of the two options as you end up moving 31GB of data on disk.