I do connect to VMs and containers all the time, I just don’t see a reason not to speed myself up on my own machines because of it. To me, the downside of typing an alias on a machine that doesn’t have it once in a while, is much less than having to type everything out or searching my shell history for longer commands every single time. My shell configs are in a dotfiles repo I can clone to new personal/work machines easily, and I have an alias to rsync some key parts to VMs if needed. Containers, I just always assume I don’t have access to anything but builtins. I guess if you don’t do the majority of your work on a local shell, it may indeed not be worth it.
From experience shipping releases, “bigger updates” and “more tested” are more or less antithetical. The testing surface area tends to grow exponentially with the amount of features you ship with a given release, to the point I tend to see small, regular releases, as a better sign of stability.