Assuming they are installed correctly what would be the next thing to look at?

 

Did all of this happen right after you did engine work?

 

yes.

 

A straightedge is your friend.

 

Not saying one way or another, but could be a sumping issue. You described overly hot engine and oil leaks. Possible o-ring for oil pump scavenge port is not seated right.

 

I really doubt that it's overheating that is causing the leak in 100 miles. Some part was assembled wrong. Maybe too long a bolt in a head hole busted out part of the head? Was the work done by a shop or some backyard guy?

 

Fresh motor build??? Have you done a leak down test to make sure the rings have seated???

 

Impossible? i blew out 2 sets on my 1200 in 500 miles and watched the rocker box to heads start weeping on the dyno before I realized my breather valves were **** and I was building excessive crankcase pressure. Literally blew the gaskets out. I haven't run Harley's breather system since. Having to pull the gas tank, covers, and all the bs just to change breather valves is just dumb. Doesn't get any dumber.
I've been running external inline reed valves since. Besides bring easy to access they do a better job at eliminating positive pressure.

 

I got a cannon ball and rubber mallet, I'd like to send you.. I've got an experiment I'd like you to performa for me..

BTW, Bet you blew out the top gasket and not the rocker base..

 

Honestly, I've never had a Rocker gasket leak issue.. I'm sure this was the leading reason... excessive crankcase pressure.. Maybe the rings weren't seated yet....