It was actually a sad day when we powered it off for the last time

No, it died not from the reboot.

It died because it’s life had no meaning anymore, after you had taken all the workload off it.

/s

I use Debian as my daily driver

Chances are that you would find Ubuntu not just more complicated, but unneccessary complicated.

Stay with Debian. It can do everything.

Can you upload by any other means, or does it always require it’s own upload mechanism?

VPS bad!

Can’t put your rings of garlic around it.