I knew i should have expected this but - Oil pan was pulled off to rest on the Front differential, new Timing cover installed (this one with the flange instead of just RTV'd to the front of the gasket) button it all back up annnd now its leaking much much more oil, from more places, How bad is it to pull the block out of these to do a proper service/ (oil pan gasket, etc)?

 

Pulling the engine out has got to be easier than removing the front diff like I did (and still putting back together) to get at the oil leaks.
Probably tore the oil pan gasket when removing the timing cover; did you replace the oil pan gasket and use RTV in the corners?

 

No way to replace the pan gasket while its resting on the differential, it will get caught on the oil pump pickup

 

Since im dropping the differential (not out but as far down as possible vs where it was when i first did this) and pulling the pan completely off this time Should i go for swapping the oil pump driveshaft? Older SBCs used a plastic pump driveshaft bushing and i dont want to be back under here for atleast a little while, and for 9 dollars melling makes one with a steel shaft, anything i should know before pulling the pump off?

 

You may want to think about just going-ahead and completely removing the front diff instead of trying to work around it. Not much room under there is there?
Do you have the steering linkage either out or moved forward? I tried to break the steering box joint and it just would not budge...and I had the steering box out a couple of years ago.

Regarding the oil pump....removal requires taking the rear bearing cap off, right? Got a torque wrench so it can be put back? I would say go ahead and replace the plastic shaft. I did not know about this or I would have.

 

The oil pump bolts to the rear main cap, but you don't have to remove the cap to replace it. It should still be torqued, though.

There are lots of manufacturers that make a shaft with a pinned metal collar instead of the plastic one. But I have not personally seen a plastic one fail.

 

Mods
Mine leaked after the timing chain was was replaced. Also had oil leak on back of engine from when the intake gaskets were replaced. I had used starting fluid to wash off oil. My thought are to have it surgery clean and use silicon to seal it up.
the starting fluid has an oil additive and left a film and silicone did not bond. That is my thinking. I cleaned the oil off again and this time I finished up with alcohol from the drug store and a cheap brush from home depot. I washed the site behind the distributer and firewall and also the timing cover area. I did this numerous times and also blew off with air; rewashed with alcohol some more, let it evaporate and resealed again with silicone; bridging the surfaces to act as a dam. Parts were not taken off. Used my gloved finger and pushed it in. Let it dry for 24 hours, this is only what I did. Used the product below from amazon. I also changed the hoses to the oil filter and gaskets. They had been leaking also. It has been about a year and 3 or 4 thousand miles and still dry. Yes I know starting fluid isn't good to use, it is what I had.
Hope this helps you.

Permatex 81878 Ultra Copper Maximum Temperature RTV Silicone Gasket Maker, 3 oz. Tube" target="_blank">Permatex 81878 Ultra Copper Maximum Temperature RTV Silicone Gasket Maker, 3 oz. Tube

Permatex 81878 Ultra Copper Maximum Temperature RTV Silicone Gasket Maker, 3 oz. Tube">Permatex 81878 Ultra Copper Maximum Temperature RTV Silicone Gasket Maker, 3 oz. Tube" /> Permatex 81878 Ultra Copper Maximum Temperature RTV Silicone Gasket Maker, 3 oz. Tube">Permatex 81878 Ultra Copper Maximum Temperature RTV Silicone Gasket Maker, 3 oz. Tube

 

as far as i can tell none of the steering components are in the way, they're all either up on the side of the block (intermediate shaft) or well in front of everything. as for the shaft it is steel, i just mistyped so it looks like i said the shaft was plastic, its the retainer bushing that is plastic,

 

Isn't the oil pump bolt held on with one both that also holds down one side of the rear cap? So no, the rear cap does not have to be removed, but both bolts have to be loosened and then re-torqued. Am I remembering this correctly? Has been over a decade since I did any engine rebuild.

 

nope, main cap goes on then the pump is held on to the passenger side of the cap, my main concern was somehow changing the pickup screen clearance if i swap the pump for a Melling M155 at the same time.