Fill clean plastic milk jugs with a funnel. Then use those to fill the engine/s. The jugs are translucent enough to see the level as you fill them. Jim
 
If you don't like the milk jug idea. Then go to the nearest truck stop and check the trash cans at the fuel island there will be several empty oil jugs from the trucks. They will be free.
 
First clean off a large potion of your work bench(this is the hardest part). Lay the 5 gallon can on it's side, on the work bench, at the far right hand side of the cleaned up area, with the spout at the top. Remove the cap from the 5 gallon bucket, and pull out the little spout. Probably best to do this before you set it on the bench. now roll the 5 gallon bucket slowly to the left, holding a smaller container, (whatever size you feel comfortable with) under the opening. All the buckets I get and do this with have a pull out spout. as you drain the bucket, roll it a little further. You can let it out as fast as you want. A lot more control than trying to pour into a little jar.
 
At orschelin for around $40 I bought some bucket pumps that just screw into the pour neck on the bucket. Well worth the money. Got one on a bucket of hydraulic oil all the time. A spare one in the shop and a spare one on the service truck. I can't remember the brands. One was red and one was gray. The gray one was much better so I bought those
 
When the pail is full, tip the pail with the spout to the top to pour the oil out. This lets the air in and keeps the oil from "glugging" and splashing all over. Same as with smaller oil containers. Pouring with the spout at the top will let you get closer to the oil fill hole and very seldom will you need a funnel.
 
That's how I do it. Only I do it outside on the trailer. Keeps any mess outside, plus you don't have to clean off the bench. :~)
 
Do as ranchingelec said, but lay the bucket on a table/shelf and turn the bucket as you fill the container you are using.
 

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