I would install a new Toyota cap, rotor, and plug wires, based on what I see on the arced points in the distributor.
As far as the oil amount goes, it's not horrible, as in, not enough to cause misfiring YET.
But, most of the Distributor O-Ring is on the EXTERIOR of the distributor itself. Your oil issue is internal, which means replacing the distributor eventually. Not a rebuildable issue....yet.
As far as doing the Dizzy O-Ring without timing it? Absolutely possible. It's how I've done a couple of them, but you MUST be cognisan of what you're doing and you do NOT have to remove the valve cover to do it.
Remove battery and battery box
Remove cap only
Clean the area around the distributor base with wire brush / solvents, etc so no crud falls in when you remove it.
Using a sharp object (large pocket knife, scratch awl, nail), mark around the outside of the slotted portion of the distribuot into the head. The mark needs to be on the HEAD.
Make a SINGLE scratch mark perpendicular to the slot on the outside of the distrib against the head. This will be the prefect line that MUST line up after you place the distrib back in.
Take a picture of the exact location of the rotor so you can get it in the exact same location when you put it back in. It is important that you get the picture from as straight on as possible.
Once all marks are made, you can loosen the locking nut on the distrib and gently (while rotating) the distrib, pull it out.
DO NOT ROTATE THE ENGINE WITH THE DISTRIBUTOR OUT OF THE ENGINE.
Cut off / break off the old O-Ring, lube the new one and install it on the distrib.
Clean the hole in the head with a solvent soaked rag.
Oil the hole and the shaft of the distrib WELL.
Insert the distrib.
NOTE: the rotor will turn when you pull the distrib. Note which direction it turns, as it will turn opposite when you reinstall.
Align the rotor in the "removed" position in relationship to the distrib body and aling the body near the position it came out. and reinsert the distrib..
The FINAL alignment of the rotor, with the body in prefect alignment with the scratch mark means your timing will be exactly as it was when removed.
If you screw this up, you can fix it, but you have to take a whole lot of steps to get there.