jdfnnl

I am preparing for a valve cover job as I seem to gather it is hard to screw up. I have the gasket, plugs, and grommets of which the current ones are somehow causing a leak. There could be a breach in the gasket, although from what I can discern, the front plug is still pliable. However, the one uncertainty I still have at this point is whether or not to silicone around the plugs or if they are sometimes installed dry.

Jimkola

By plugs I'll assume you mean the 1/2 moon seals.
The FSM does recommend a small amount of fipg/sealant be placed on the curved section of the plug. Make sure the area on the head is free of any oil residue before using sealant.
The torque spec on the valve cover nuts is pretty light, about 48 inch/pounds iirc. Don't overtighten.

scope103

https://web.archive.org/web/20120813...68cylinder.pdf page EG2-80
As I read the FSM, the sealant goes just at the edge of the 1/2 moons, where the valve cover gasket has to make a sharp rt angle turn. 48 inch-lbs is correct. Your 1/2" drive torque wrench won't go that low. Yes, it's worth dropping $19 for a 1/4" drive torque wrench. If you over tighten the bolt you'll just pull the threads out of the aluminum head.

Jimkola is not kidding about removing all oil/dirt residue where you're putting the sealant. I've had to redo this job at least once because the rtv wouldn't stick.

osv

you have the 22re, right? toyota has improved their fsm over the years, for instance in their 1987 fsm they did a much better job of clarifying how and where to put sealant on the valve cover gasket, vs. the half-baked job they did on the 1985 fsm... this 1987 fsm shot is not the best pic, but i think we can see enough to tell.

i have not had good luck with aftermarket valve cover gasket sets, consider replacing all of the rubber gaskets including the half-moons with factory toyota.

as an aside, when crankcase pressure is excessive it can blow oil out of places you'd least expect it.