Update version and move to larger SD card

I’m running an older version of HA (0.92.1) on bare-bones Ubuntu on an 8 Gbyte SD card. It has been working fine, and I’ve therefore been reluctant to update unnecessarily, but I think the time has come when I have to update my HA version and deal with any breaking changes. I’d like to at least double the SD card size at the same time.

So any advice on what’s the best way to upgrade from 0.92.1 - one version at a time? All at once? or just wipe and start over fresh? I probably have at least 30 devices representing more than a dozen integrated services (Kasa, Tuya, Ring, Amazon, Google, Homekit, Sonoff, Sonos etc.), and a lot of Node Red automations.

Restoring a card image backup to a larger SD card also seems to be problematic. It seems that most questions about that either don’t get a response, or a complicated set of post-restore Linux partition adjusting instructions. Are there no backup utilities like those for Windows that can automatically extend partition size when restoring a backup to a larger drive?

Any help or links appreciated.