D2 Steering clutch release bearing

I have a D2 5U that I lost the left steering clutch on. After removing a few heavy pieces of metal from the machine I realized that my clutch packs were in great shape but the release bearing was shot. So I ordered a new bearing from CAT and installed it. I've been back to pushing snow for a few days now. As my luck sucks now the right side is losing adjustment fast (same as left before it went out). It's not a surprise really. If the left wasn't getting oiled, the right wasn't either I'm sure. So here's my current dilemma, why not install a sealed bearing? I usually prefer a serviceable bearing but this oil system seems flawed. Anyways I was hoping to get some of that good "old timer" input here and avoid having to learn from my own mistakes.

Later tractors had greaseable bearings, much better.

can the oil type lube system be converted to grease type in the field?

I think so, wouldn't require any machining I'm pretty sure. The extent to which it would have to be disassembled depends on whether the oiling system used pressure hoses or cups and tube. If the latter, the final drive and steering clutch housing assembly would need to be removed to enable installing a grease pressure flexible tube from the top of the transmission case down to the throw-out bearing assembly. Might be able to do that without removing the inner steering clutch hub.

Mine has the drip tube and oil cup. I've thought about converting it to greaseable. Maybe I'll go ahead and order the sealed bearing then take a deeper look into making it a greasable system once apart. If I do, I'll take pictures and post them. Maybe it'll help someone in the future.