"Chain maintenance sounds like a real chore..." "I hate oil flinging everywhere, and I'm not sure how to do it properly."
Does that sound like you?
I used to hate regular chain care and oil fling too. At one point I even escaped to a maintenance-free shaft-drive bike (ha). But the shaft-drive bike was heavy and hard to manage, so in the end I came back to a light, fun-to-ride chain-drive bike.
After more than 20 years of riding and a lot of trial and error, here is the lubrication method I've settled on: it doesn't make much mess and takes about 10 minutes.
Skipping chain lubrication shortens the life of your chain and sprockets.
1. Why lubricate the chain? What happens if you don't
"Chains don't break that easily, so now and then is fine" — is that what you think? If you neglect your chain, the following can happen.
- Grinding or clattering noises while riding
- The chain looks grimy
- More friction, so the bike feels heavier to ride
- In the worst case, a risk of the chain breaking while riding...
On the other hand, lubricating regularly brings these benefits.
- Lighter running: just turning the rear wheel by hand, you can feel how freely it spins
- Longer chain life: less wear, so the chain and sprockets tend to last longer
- Spotting problems early: you look closely around the rear of the bike, so you notice tyre wear or nails and other objects stuck in the tyre straight away
2. How often and when to lubricate the chain
For the interval, check your bike's owner's manual or the chain maker's guidance. Also, after riding in the rain is a good time to lubricate.
My recommended time is "straight after getting home from a ride, while the chain is still warm". When the chain is warm, the oil is thinner, and I think it soaks more easily into gaps such as between the rollers and bushes.
3. Tools and oil that make chain lubrication easier
Here are two items I use that make the job go smoothly.
1) AZ precision oiler, 15 ml DX, with a soft needle nozzle
Spray chain lube is convenient, but it tends to fling onto the wheel and tyre. With this oiler you can apply oil exactly where you want it, "one drop at a time". The best thing is that the metal nozzle can be bent freely, so it reaches into narrow gaps that are hard to get at.

2) A.S.H. GEAR PSE 75W-90 (part-synthetic gear oil)
You might think "Shouldn't it be a chain-specific product?", but I use gear oil left over from when I rode a two-stroke. In my use, the chain moves smoothly and it doesn't get gunky like spray lube.

[If you don't have a centre stand] Handy tools
If your bike has no centre stand, a tool that lifts or turns the rear wheel makes the job easier.
- Maintenance roller stand (lets you turn the wheel easily)
- Paddock stand (lifts the rear simply)
4. How to lubricate a motorcycle chain (4 steps)
Here are the steps. Once you're used to it, it takes less than 10 minutes.
Step 1: Make the rear wheel free to turn
Put the bike on its centre stand or use a roller stand so that you can spin the rear wheel by hand.

Step 2: Put one drop of oil in each of the chain's "four spots"
This is the key point. Rather than pouring oil over the whole chain, aim one drop at each of the "four gaps" on every link.

- The gap between the outer and inner plates (left side)
- The gap between the outer and inner plates (right side)
- The gap between the roller and the inner plate (left side)
- The gap between the roller and the inner plate (right side)

You might think "Four spots on every link? That'll take forever...", but with the AZ's fine needle nozzle you can drip, drip, drip at a steady pace, and it's over sooner than you'd expect.
Step 3: Turn the wheel to work the oil in
When every link is done, turn the rear wheel forwards by hand about 10 times. This spreads the oil between the rollers and bushes and between the plates.
Step 4: Wipe lightly with a rag
Finally, gently wipe off excess oil from the surface with a rag. Too much oil left on the surface will fling off while riding and dirty the wheel. The oil you need is already in the gaps, so the surface just needs to feel dry to the touch!
5. Summary: regular lubrication for happier riding!
It may feel like a chore at first, but once it's a habit it's not much trouble. Above all, once you've felt how light the rear wheel spins by hand after lubricating, you'll look forward to the next time!
A 10-minute job to make your chain last longer and ride safely. Give it a try after your next ride.
To keep flung chain oil off the rest of the bike, I also extended the chain guard: