Dipstick removal
 

I want to remove the dipstick to replace the o ring, but i'm unsure if the oil has to be drained or not.

Thanks.

The oil does not need to be drained. Pull the tube the oil will drain to the correct level all by itself.

Lift the front or drive it up ramps. That'll give you more than enough, even if overfilled a smidge.

I pull the dipstick out every time I change the oil with this to use the larger tube and it never leaks oil. https://www.amazon.com/America-5060T...omotive&sr=1-8
Just make sure your car is on level ground.

It would be nice if that container was clear with marks at 1/2 quart levels so you can see that you've removed the full amount.

Yes it would but the metal container is stronger than a plastic one. I can tell by the weight of the container when it has removed all the oil; and I always have an empty 5 qt jug available to dump the container in to before I add fresh oil to also make sure I have sucked all the old oil out.

Is it leaking oil around where the dipstick goes into the engine block?

Yes it is.