Knock on wood, only been stranded once, broken throttle cable on a '99 Road King. HD's are as reliable as most everything else, car or bike. Haters will hate. Never any issues with my '08 Ultra or my '16 CVO RGU. Unfortunately, your oil pressure observation is dead on. My '08 did the exact same thing. It was a tad better when I dumped the HD Syn3 for Amsoil, AND it ran cooler and quieter.
I fully disagree with your statement in bold. I have run several GMC trucks well over 150K miles, A Range rover over 100K, a Xterra over 200K. The Nissan Xterra is the only one that ever left me stranded, that happened at 218,xxx miles, harmonic balancer failed. Nissan paid half the repair bill.
I am a Harley Fan. I currently have two CVO's and a Fatboy, plus my wife has two. I have had Five CVO's.
09 SERG, Failed compensator, then Failed lifer at 46K miles while at dealership, required rebuild.
12 SERG Voltage regulator failed at 6K miles, left me stranded in IN on a Sunday. No dealer open with in 300 miles. Hydraulic clutch master cylinder failed with just over 12K on it, stranded again. Compensator failed.
13 SERK, no failures, but I rebuilt the engine at 1500 miles with better parts. So far no issues.
15 SERGU. Water pump failure, Catastrophic lifter failure at 44K miles, required a new engine
17 SESG, 18K miles, so far so good
I have never had a car or truck that has had lifter failure, or other drive train failure. Nor a regulator failure at less than 50K miles.
All most all my trucks and SUV's have gone over 150K before I have had mechanical failures.
That said, I have yet to find a motorcycle I like better than my CVO's.
Would look hard at BMW bagger if they had a lager dealer network.