I have the Lasdrop dripless, the type with the rubber lip seal like the front main seal on an engine. Dead simple, no bellows to fail, and it does not leak. The rubber seal needs replacing now and then but they're like $5 at NAPA. When it does fail it just drips. I'm pretty happy with it. It's been in the boat about ten years and I've only replaced the seal once. Same problem as and dripless seal getting the shaft out of the coupling. I followed the recommendation of putting a spare seal on the shaft between the box and coupler so the seal can be replaced without pulling the shaft so I haven't had to pull the shaft again.
And yes the hose on any stuffing box can fail. On my previous boat the rudder stuffing box (aluminum, really bad idea) seized to the stock over winter and when I tried to turn the wheel it ripped the hose apart. That was a bear to fix.
And yes the hose on any stuffing box can fail. On my previous boat the rudder stuffing box (aluminum, really bad idea) seized to the stock over winter and when I tried to turn the wheel it ripped the hose apart. That was a bear to fix.