On my '93 FatBoy, I ran HD 20/50 for the first year, then moved to Red Line. 20/50 for the engine, and MTL and 75/90 for the Tranny and Primary. That was 45K miles ago. No problems relating to lubes. I have EXTREME faith in Red Line. Used to work with a SCCA Trans Am team based here in Phoenix. The first race I went to was at Sears Point and we ended up running the last 8 laps of the race with NO WATER in a small block Chevy... At the end of the race we quickly cut the belt off the external oil pump and put a drill on the pump to keep oil circulating... That small block sounded just like a Harley cooling down. Thought we'd need a new motor for sure. BUT... after we tore the motor down... nothing, the main bearings were ok, the block didn't crack, we put the engine back together and ran it 3 weeks later at Long Beach. The crew chief has had it in his '90 Chevy pickup and has had NO problems on a 350 with well over 500K miles on it. That's some GOOD oil. But it's hard to find and it ain't cheap.
The '01 Road King was dino oil when I got it, but I switched to SYN3 when it came out.
The '00 SERG is dino oil... I've only had it about a month... having the top end done. Compression wasn't what it should be and the leak down test was in the 13 to 15% range... Somebody didn't know how to store a bike for winter (the bike came from WI). The plan is to seat the new rings with dino oil, for one lube cycle, then switch to SYN3. One things you have to remember is to vary the rpm's when breaking in an engine. And gas it once in a while, the quick gassing will put additional pressure on the rings and push them out to the cylinder walls for a good seat.
Back when synthetic lubes were new. It was recommended to break the engine in before switching to synthetic. But with new engines.... Well, if Harley puts SYN3 in the new SE's, I'll trust them. Their engineers know more than I do. 8-)