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Dented oil pan going over raised manhole cover. Immediate replacement or can it wait until winter?

You're missing the dust cover/ inspection cover at the bottom of the bell housing.
It extends beneath the starter as well, so someone left it off.
Don, any idea the risk of using a aftermarket dust covers that I can slip on without needing to take the starter off? After browsing for awhile it looks like these are my only two options…plus it looks like neither come with bolts.

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Hard to tell the depth from pictures without a straight edge across it. Not sure a stock oil pick up has a lot of clearance to the pan bottom.
IMO, it would be a good idea to pull the pan especially if you know the pickup is close to the bucket bottom. If the pickup screen is breached, it may be possible for the oil pump to pick up debris large enough to lockup your oil pump.............. at any time in your travels.

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Might also be good to get the cover back on the trans.

It may just be me but I can’t see having the strainer bottom touching the bottom of the oil pan (in yellow). A 1/4” of clearance sounds much better to me.
 
With the factory pick, I make mine all touch.
 
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@AR67GTX Look over post #9 again. The service manual says to have it touching. I've seen and imprint of the pickup in the residue at bottom of the pan many times. Doesn't hurt anything they have a cut out in the factory pickup for adequate oil flow.
 
I think you’re worrying way too much about nothing. If it bothers you that much, drop the pan. It’s only a few bolts.
I was having a problem probably 1991-2. Under hard acceleration the engine stumbled. Read an article about the fuel pump rod might be worn down.
Car was sitting outside on gravel in the fall. I went out, pulled the fuel pump off, ended up dropping a bolt into the pan. Jacked the front end up.
Dropped the oil pan got the bolt which sat on top of the oil pan pick up. Was it easy no! Necessity is the mother of invention. Re bolted the pan,(and Bob’s your Uncle, it didn’t leak.
Ended up that the short fuel line from filter to the car had a slight crack. Under acceleration it would suck air in, and it would stumble.
Surprisingly we pulled a crank down camper trailer to Aurora Missouri and back. Close to 1600 miles each way.
One of the 67 Charger 440 auto’s.
 
To the OP: That's not much of a dent. You're fine.

I did much worse with a floor jack and then looked inside with a borescope. It was not plugged/obstructed. .
 
@AR67GTX Look over post #9 again. The service manual says to have it touching. I've seen and imprint of the pickup in the residue at bottom of the pan many times. Doesn't hurt anything they have a cut out in the factory pickup for adequate oil flow.

I read it right the first time and understood. I’ll stick with the aftermarket suggestion of 1/4” in case of the random oil pan dent as in here, and to be sure it has plenty of suction area.
 
I read it right the first time and understood. I’ll stick with the aftermarket suggestion of 1/4” in case of the random oil pan dent as in here, and to be sure it has plenty of suction area.

I believe the aftermarket suggestion is for an aftermarket pick-up that is a completely different design. Those do need bottom clearance.
 
Don, any idea the risk of using a aftermarket dust covers that I can slip on without needing to take the starter off? After browsing for awhile it looks like these are my only two options…plus it looks like neither come with bolts.

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You didn't mention your engine but yours looks like the BB 727 version (the easy one)...the first picture in the ads you posted..
They take four 1/4-20 bolts half or 3/4" long.
 
How about draining the oil, leave the plug out, shoot a tad of starting fluid into the oil pan thru the plug hole, stand back, light it, and let us know how it works out.
Probably should video it, it will make you famous on Utube. :lol:
Of course at your own risk.:bananadance:
Another one of my stories closely related to this comment. Back in the late 70's I bought a really nice 73 2 dr Chrysler New Yorker Brougham with a transplanted 383-2 engine. It didn't run, owner said he thought there was a hole in a piston. I started getting ready to pull the engine and I thought-what have I got to lose. I put a battery in it, hooked up a few things and gave it a very healthy shot of either. I turned the key and BOOM!!! It blew the oil pan, valve cover gaskets completely out, it bulged the oil pan, the valve covers and the valley pan. Yep-there was just 1 hole in 1 piston.
 
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