the issue i've had with the turbolube types is the rear seal not holding up... when oil heats up it expands and that builds pressure in a sealed system... the easiest place for the pressure to go is between the rubber seal and the shaft at the rear of the hub... if it does this, even if it leaves you with enough fluid to cool the bearings, water will leak in through the failed seal when loading and unloading a boat creating a mess inside the hub...
now i pull my boats quite a bit - i'm guessing between 5 and 10,000 miles per year, on long trips, in the heat of the day... i'm probably way over the average user... trouble is you have to watch the color of the fluid very closely through the cap, which isn't the easiest on the setups i've had, for changes in color... water will initially mix with the fluid and make it look milky... left inside it will start to rust the bearings and races and turn an orangish color... if they fail at highway speed, you're gonna b calling your insurance man...
looking at an oil level or color is really the only check with an oil bath system as they tend to torque the nut really tight, whereas with a greased hub you just give it a shake to see if it is tight, and feel the outer hub to check for heat... if it is tight and cool, you're good to go... with the oil bath, you'd better b checking the inside of the hub all the time to see if it's leaking cuz that's about the only tell other than color...
the other problem is they are not a standard size bearing(at least not when i had trouble)... with a standard grease hub assembly, most of your bigger cenex stations have bearing and seal kits hanging in the store that will at least get you home... most trailers have a 1 or 1 1/4 or 1 3/8 inner and outer bearings - some run a different inner and outer... they are available cheap everywhere... i have a whole extra hub with bearings and races and a seal and grease in the truck at all times for my boat trailer... with a jack, hammer, needle nose, screw driver and channel lock i can replace a hub along side the road in 10 minutes with little or no mess - with the oil bath - not so much...
i'd pull a 30 year old trailer coast to coast with $100 worth of parts and tools with more peace of mind than pulling an oil bath system across the state...