My current boat has a drip-less. It was on when I purchased it, otherwise I would keep to the old stuffing box technology.
I'm pretty far out on my own mooring so I rely on neighbors in the mooring field to keep an eye on things.
If/when the time comes, I'll probably go back to a traditional stuffing box with the high tech stuffing material.
My mast is keel stepped so my bilge is rarely completely dry so what's the point in pretending