Sooo, the leak down test was less than 20%, which is within Harley's spec's (Harley supposedly says up to 25% is acceptable on the 4 valve M8 especially with 40K.

), compression is 230 per cylinder, and bore scope apparently showed nothing out of the ordinary, so mechanically everything seemed to be within spec. Time to look elsewhere.
Checking the tune with my TTS Mastertune the young gamer tech named Wade (who is my new idol) found that the tables were way out of whack and went to work. Apparently there was a major lean spot at the rpm range in question and the adaptive fuel values were all over the place. He changed my plugs and rebuilt my entire main fuel table (which with TTS is no small feat and very time consuming apparently) while doing about 10 dyno pulls to get some great results. Then, after reading a thread on here, I had him upgrade my intake to the Screamin Eagle 55mm intake and 5.1mm injectors and re-tune it. He then took it out for a 35 mile real world ride and the chart below is what we ended up with doing 5th gear runs. So a big thanks once again for all of the great input from the members here.