I did not understand at first, but the "engine" light does in fact come on for a few seconds after its up and running, so there is a diagnostic code or error recorded. Thats great information, duh, I did not know how that worked.
At least maybe it not a great mystery, I don't have a clue as how to conjure up those codes, but at least I can take it somewhere and they can read the problem right away. Its usually the labor that kills you on the repairs these days, the parts aren't so bad.
They can read the "code" but not always the "problem". If it was that easy, anyone could do it.
I would invest in a genuine service manual. Even if you don't do your own work, it gives you some insight as to what is going on. Makes it harder for them to sell you excuses.
1999 had a bank angle sensor problem because the bracket was too flimsy and would cause the sensor to tilt and shut off the ignition. There is a bulletin for repairing the bracket.
Not being sure of myself, I took it to a Harley dealer, they reported the Crank Sensor is in fact DOA. Its not in stock, they must order it(?) so it will be early next week before its actually repaired. I figure its worth it, since I would have been guessing, don't want to be unsure of it 100 miles from home. Thanks for the input everyone, case closed.
I to have a 99' FLHR, and experienced ( from what you've described ) about the same issue. It turned out to be a faulty bank-angle sensor ( about $38 ). My bike would just die, sometimes would start right back up others it took a few tries. I took it to my local independent shop and they finally isolated the problem. Changed the sensor and have never had another problem. (PS, I bought two. They don't take up much space so I keep a spare in my hard bag toolkit. Good Luck!