That operation SUCKED!!

I ended up drilling out the dowel pin location holes to allow better clearance: that was the only way I could get this done.
@Reed: yes, I would have tried to install the lower bolts and have them help to compress the gasket IF I had been able to get those lower holes lined up with the pan correctly. Maybe loosening the first three or so oil pan bolts on either side would have allowed me to drop the pan just enough to give clearance for that gasket, but I don't know how people loosen the pan bolts with the engine in the car, access is so tight.

My main concern in this operation is leaks. A) from the rubber corner blocks, and B) the front seal. I wonder if the corner seals will leak if I don't spread RTV on the seams (wasn't able to get any inside, after re-installing them). And the front seal should be centered correctly, but it might be off a hair because of the way I had to install, I couldn't 'float' the cover as Doc suggests in his article, once you drill out the locator holes.

If anyone has a helpful suggestion on how to make sure I'm going to be leak-free in these two areas, lemeno. I'm finishing this thing.

I had a leak in that area after some " professionals" built an engine and line bored a block and never realigned the timing cover. The seal leaked and was replaced by them under warranty....it leaked again. I fitted an original Mopar type seal until I built up another engine for the car. The Mopar seal seems to be more forgiving with misalignment and never leaked despite a noticeable misalignment. I had to unscrew quite a few of the sump bolts to get enough room to get the cover back on,with the help of RTV it held tight. Be careful the rubber seal on the lower cover doesn't slide,if those little mounting lugs on the seal break off it can leak bad. Now you have drilled out the holes in the cover Im pretty sure there will be a seal misalignment,perhaps it's worth trying to push/ lever down the cover downwards to try and centre the cover on the dowels a little better?

Update: operation is done. Timing cover is centered as close as possible. Damper is properly and completely seated. The water pump pulley now lines up perfectly.

Good to hear!

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1964 Dart GT