In short, I think ignorance is the simpler answer ;)
Not even then. The prospect of making an occasional mistake, while low, is clearly much higher than when you are selecting the disk using its name. Being experienced doesn't excuse you from the responsibility of using a less risky tool.
Usually on Linux I only use /dev/disk/by-id/foo in scripts and config files. But using it when doing routine stuff with dd is a pretty good idea too.
It’s too bad that macOS and FreeBSD hasn’t anything similar to my knowledge. And since I use both of these operating systems so much, and so often for things involving dd, I think in my case I don’t gain much from doing by-id for dd on Linux unfortunately.
Even this is faulty solution. By default, it only lists the devices with their "/dev/sd*" names.