

I run a gluetun docker (actually two, one local and one through Singapore) clientside which is generally regarded as pretty damn bulletproof kill switch wise. The arr stack etc uses this network exclusively. This means I can use foxyproxy to switch my browser up on the fly, bind things to tun0/tun1 etc, and still have direct connections as needed, it’s pretty slick.
Seems like data integrity is your highest priority, and you’re doing pretty well, the next step is keeping a copy offsite. It’s the 3-2-1 backup strategy, 3 copies, 2 media (used to mean CDs etc but now think offline drives) 1 offsite (in case of fire, meteor strike etc), so look to that, stash a copy at a friends or something.
In your case I’d look at getting some online storage to fill the offsite role while you’re overseas (paid probably, but a year of 1 or 2 Tb is quite reasonable) leaving you with no pressure on the selfhosting side, just tailscale in, muck around and have fun, and if something breaks, no harm done, data safe.
I’ve done it for what seems like forever and I’d still be worried about leaving a system out of physical control for any extended period of time, at the very least having someone to reboot it if connectivity or power fails will be invaluable, but talking them through a broken update is another thing entirely, and you shouldn’t make that a critical necessity, too much stress.