So I've got a rather large oil leak on my Yblock that's been going on for awhile, but I finally got her up on ramps to try and track it down. Thing is she's had old oil coating the bottom of her engine ever since we got her so I dunno.
From what I can tell the oil seems to be sliding down the brim of the oil pan on only the drivers side, from around the oil sender, back to the bell housing and then dripping off that onto the ground. I was worried it was the infamous main seal leak for a long time since I could tell it was dripping from around where the engine and tranny connect but upon inspection it's coming from somewhere forwards of that.

Around the base of the oil sender is dry, and I don't THINK? It's the oil filter? It's hard to tell since the bottom lip of it is behind the lip of the oil pan.. if it is it's coming out RIGHT on the bottom of the filter where I can't see, could it be a bad oil pan gasket? Would the oil level be high enough in there to be flowing over the top? I guess the car is up on ramps so the incline could tip the oil in there towards the back pretty high. What do you guys think in your expert opinion?

I'd start by cleaning the engine, at least on that side.  Seems to me it would be near impossible to find the leak(s) without cleaning all the existing oil off.

No offense intended, my bird was worse than that when I bought it. You need to find a guy with a lift and a steam cleaner, and clean everything off. Otherwise, you’ll never be able to chase anything down. If it’s still a road draft tube, consider a pcv system.

miker
55 bird, 32 cabrio F code
Kent, WA
Tucson, AZ

So am I basically out of luck until I do some cleaning? : /
Well I like to keep things on the cheap if I can, can I clean it myself with a scraper and such?

After scraping brake kleen is pretty good for the remaining wet oil. Then you may be able to find exactly where the oil is coming from. Oil leaks can travel a ways before you find them.

Y's guys rule!
Looking for McCullouch VS57 brackets and parts. Also looking for 28 Chrysler series 72 parts. And early Hemi parts.

MoonShadow, 292 w/McCulloch, 28 Chrysler Roadster, 354 Hemi)
Manchester, New Hampshire

Google "constant loss oiling system", you are fine, clean oil in the top, dirty, out the bottom

Lol I can see what you mean there, but it's not like the Yblocks were designed to function that way. Plus if I'm going to spend $40 on Lucas Classic Car Oil I'd rather it not dribble all out on the road you know?

Just a guess, but it looks like maybe the oil pump or oil filter, but like the others said, without cleaning the old oil off you are just guessing.  there are special dye's made you can put in the oil and then run the eng. then look for where the dye starts showing up. it is made in different colors. some must have a black lamp to be seen. I have not used any of this in years. I used to use it in boats, and heavy equip. where it was hard to get at most stuff to even see what was leaking.

Yeah I got some of that dye and put it in the oil a few weeks ago, did some driving, I couldn't see anything though, it was the kid with the gun and with the glasses.

Looks to me like a classic road draft breather plugged up and leaking.