My newest Harley is a 1974, so really can't speak to the last 45 years...
The Shovelheads, Panheads, Knuckleheads, Flatheads, were never "reliable" in the sense of turn the key and go like Jap bikes. They were, however, simple enough that a rider could usually keep them running.
I know the early carbureted Evos were pretty bullet proof.
Then came fuel injection and computers.
What could go wrong?
In the late 60's and early 70's my kid brother rode his Harley for kicks and looking good.
On his many trips all over the country, he rode his Gold Wing.