Do they work? Are they problematic? What goes wrong? Have they saved your bacon? Do you still pack the bearings normally, or do you put them in dry and let the Bearing Buddy pack them?
It's time to go over the wheel bearings on the trailer, and I'm thinking about these.
I use my foodsaver to pack bearings. Smear copious amount of grease all over the outside of the bearing, place in foodsaver bag and vacuum seal. Presto...packed bearing. Great for storage also.
Had them on all of the boat trailers I have owned. Always replaced the wheel bearings (or at least inspected them) when I got the trailers, cleaned the bearings, and manually packed them with Sta-Lube waterproof grease.
When I pulled the boat out, gave it a couple of shots of Sta-Lube from a grease gun until a bit came out of the rear seal. Only problem is that this stuff is really waterproof - use nitrile gloves when you are packing the bearings. Also, makes a bit of a mess on the back of the hub, but it will wipe off.
Doing this, I have never had a trailer bearing fail or even get warm. I have had a couple of trailers rust out from under the boat from salt water, but the bearings were still fine when the trailer went to the dump.
Interesting idea on the food saver. I use my hand. The bearings are packed solid, so I don't have to waste a bag to do it, and it is actually easier and faster than using a bearing packer. Cleaner too, with less mess/waste.
Now, the bearing buddy things, those look interesting from a maintenance standpoint. Just squirt some grease in them and worry less. Never tried one.
I have had bearing buddy things on many trailers. Two downsides that I can see.
If it is a boat trailer, I don't particularly like them unless you always keep them packed full. They often get water in them (they get warm on the highway, then you back them into the cold water, things shrink, and it sucks water in.) With a traditional setup, you can have a tablespoon of water in the hub and it doesn't cause havoc. It just hangs out in the middle and often times you get enough heat that it evaporates out before major damage. With bearing buddies, if it sucks water in, it stays in the grease and whips the grease into an emulsion.
For non-boat applications I find them to be great. Some people claim that the excess grease holds heat and can cause a questionable bearing to seize faster without anywhere for the heat to go, but shame on that person for having questionable bearings 
I'm keen to try those oil bearing setups. The axle stub is gun-drilled and you fill it with 90w gear lube and it has a clear polycarbonate dust cap so you can monitor levels and condition. You can also get a similar gun-drilled setup with a grease fitting (of course requiring retrofitting that spindle onto your axle.
The problem with bearing buddies is that they aren't designed for lubrication, they are designed to use the spring to keep positive pressure inside the bearing side of the seal to keep water out. So while they can do a good job of keeping the outer bearing packed they only really do anything for the inner bearing if the entire cavity between the bearings is filled with grease. Then, whatever junk the grease picks up from the outer bearing gets pushed into the center and eventually into the inner bearing. Meanwhile the entire cavity being filled with grease tends to heat up and eventually the oil comes out.
The newer alternative, sure lube or whatever, puts a grease zerk on the end of the axle and injects it between the inner bearing and the seal. Pump enough grease in there and it will go through the inner bearing, fill the cavity, then through the outer bearing and out onto your shoe. This at least puts the new grease on the more heavily loaded bearing and the used through the less loaded outer bearing. Still the same problem with heating up due to the center cavity being full of grease.
For a while you could get hubs with grease zerks on the back side of the flange straight into the cavity between the bearings. Then new grease for both bearings! And the cavity filled solid with grease.
If you want your cavity pressured to keep out water, get a bearing buddy. If you just want to defer maintenance, spend the $ buying a spare set of bearings, lubing them up, and store them ready to go with a couple spare seals, cotter keys, and a cap on the trailer somewhere.
In reply to EastCoastMojo :
That is the koolist Idea I have heard of, And will look for a unit at a Yard Sale to give this a try !
Like Dr.Hess The Old way is My way ,By Hand. I have a Couple Packers, the stem is broken off Both Because I have to Stand on the them to Pack the Bearings, Was Gonna try Micro waving the Packer and Grease next Time to make it Flow ? better . Setting up wheel Bearings is something I spend a Generous amount of Time On.
Find your Power where You Can
That actually answers another question for me, which is the hive's opinion of putting grease in the middle. I was taught to put grease only on the bearings. It seems like most agree.
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