So I think it comes down to personal preference. This is going to sound a bit silly, but to me, running things in VMs feels like living in an apartment. Containers feel more like living out of a hotel room.
I know how to maintain an apartment, more or less. I've been living in them my whole life. I know what kinds of things I generally should and should not mess with. I'm not averse to hotels by any means, but if I'm going to spend a lot of time in a place, I will pick the apartment, where I can put all of my cumulative apartment-dwelling hours to good use.
I might tweak the apartment metaphor because I think it's generous to imply that, like a hotel, Docker does everything for you. Maybe Dockerless development is like living in an apartment and working on a boat, while using Docker is like living and working on a houseboat.
There is one thing I definitely prefer Docker for, and that's running images that were created by someone else, when little to no configuration is required. For example, running Postgres locally can be nicer with Docker than without, especially if you need multiple Postgres versions. I use this workflow for proofs of concepts, trials, and the like.
I personally run a bunch of software I've written, as well as open source things. So for me docker makes everything significantly easier, and saves me installing a lot of rubbish I don't understand well.
I then booted into a new fresh clean debian environment, mounted my disks, and:
cd /opt/docker/configs; for i in *; do cd $i; docker-compose up -d; cd ..; done
voila, everything was up and working, and no longer tied to my underlying OS. Now at least I can keep my distro and kernel etc all up to date without worrying about anything else breaking.Sure, I have a new set of problems, but they feel smaller.
Like, legit, this is the whole point of docker. Application/service dependencies are no longer tied to the server it is running on, mitigating the worst parts of dependency hell.
Although, in your case, I suppose your tolerance for dependency hell has been quite high ;)
I get what you are saying, but note a word of caution - kernel upgrades can break container runtimes: https://github.com/containers/podman/issues/10623.
At some point I moved individual containers to other machines and they work perfectly. VPS, NUC no matter what.