Can’t be afraid of doing maintenance just because some people don’t do it right and have issues. There’s a centering tool that comes with the ACDelco rear main seal that ensures it gets installed right, if you follow directions you’re good to go. I guess if you buy a crappy main seal like a Dorman you deserve what you get. But I’ll never be afraid to replace any and all wear items with OEM quality when they’re buried like that. I mean, your trans went out at that mileage so who’s to say the main seal isn’t far behind. That’s my thinking anyway.
When I saw the condition of the rear cover gasket, I'm surprised that not more of them are leaking. The gasket material became flattened over time and heat cycles so that it was no longer making a seal. I had more leaking from the cover than the rear main itself.
Also, Mark is right that you can't be afraid to replace the seal (done properly). There appears to be some debate about whether to lubricate the crankshaft side of the RMS or not. Teflon impregnated seals are not supposed to be lubricated in any way, shape, or form. The Teflon transfers from the seal to the metal of the crankshaft. Felpro claims that if you lubricate it, it can leak within miles. I have also heard it said that Felpro admitted that lubricating the crankshaft side of the seal doesn't cause it to fail, you just don't get the benefits of the Teflon. The main reasons for failing is improper installation of the seal itself. I gather it is extremely easy to get the lip of the seal pushed aside during installation causing instant leaks.
The other cause of leaks is when guys torque down the pan-to-rear-cover bolts first. This pulls the rear cover down off center from the rear main seal. The rear cover bolts should be tightened first to keep the rear main centered when you torque the rear pan bolts.
Anyway, what's done is done. Hopefully your rear seals will last a long time.