I cleaned up the area right under the pulley before testing. If the video doesn't work, I tested with the glove, it sucked it in, and a new drip of oil started after a couple revs.

 

Well having vacuum is good, so it is either coming through the ID, OD, or the cover. I have seen some cracked covers because of broken oil pumps. If it is coming through the ID, likely damaged surface on the balancer shaft. To seal the od, coat the seal with a thin layer of silicone before driving it in.

 

Last go around I really took my time and cleaned all the surfaces and added a thin coat of oil resistant silicone around the OD. I also pressed in the seal using the pulley bolt rather than tapping it in with a hammer. I got the speedi sleeve in today hopefully that will do the trick, but I still think it's the cover. I'll really celebrate if it takes care of the problem.

 

Speedi Sleeve for the win. I've never been happier to be wrong about what was going on. I really, really, really didn't want to have to pull the cover.

THANKS TO EVERYONE for the suggestions and help pointing me in the right direction!

 

Speedi Sleeve is the GOAT. I'm a two is one, one is none kind of guy, so ended up buying another SS for the future just in case they ever stop making it.