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I'm not afraid of that risk and just try to mitigate possible outage of services longer, than expected (I hope to refresh the server in 1 day, but as with everything new, it can take longer).
What do you mean by "direct upgrade"? I want to have every direct modification done on OS to be done troguht ansible playbook on refreshed build, so my assumption is that I have to purge / start from new SSD in that case.
Replace the drive and start new but anyway because they're docker containers you can mount the old drive and temporarily run them again
how many devices do you need to update?
ansible wants to have a home base and an inventory of devices to manage. for example, if you have a flock of Rasberry Pi's and a server stashed under a desk somewhere, yes, ansible is 100% going to simplify your life.
ansible mgmt from a device to that same device.... It might be just as easy to make backups and track your file deltas. the temptation is to use ansible so you remember what changes you made, but it can be a pia when you need to do a quick shift and have to go thru the playbook (unless you have playbooks on the ready).
I've got personal laptop + mentioned Dell Wyse 5070. In near future (months) I'm thinking about extending to another home server client.
I know using ansible in that scenario will be somehow harder than direct ssh, but I want mainly to learn the process (for future work possibilities) and have that extended control of the changes on the bare OS.
Awesome, go for it! ansible (more or less) is directed ssh. inventory, role, playbooks + templates, etc; for learning, definitely go for it! if you were to roll your own automation framework, you'd end up w/ansible.