Ha! I'm the worst to take marital advice from. I barely made it over 40 months. LOL!
Check the pushrod area. When I did the 1250 kit on my 2016 Sportster, one of the pushrod orings "shifted" and wasnt sealing properly. It was baffling at first, because at idle, no issue... but go for a test ride and it was puking oil. Got it home, cleaned it up, then started it up to check for a leak.... nothing. Went for a quick test ride, and before I got out of the neighborhood, oil was all over the place.
Also, I think there is an oil pressure switch in that area. Make sure its not dribbling oil. You may have to rev it up to reveal the leak.