Hey Jay,
Sorry to hear of your troubles.
I had the exact same thing happen years ago with my 1991 Heritage, and sometimes it is the simplest things that get us.
I'm out for a ride with my buddy and going through a small town another joins in at the back. About 10 miles up the road, cruising along enjoying the day, my bike just shuts down. I pull over, my buddy follows, and the tag-along keeps going up the road. My buddy and I can't figure out what the heck happened to make my bike just quit like that. We go over all the usual things ensuring the plug cables are seated correctly, check the battery leads, etc. and could come up with nothing - and yes I had lots of fuel.
After about 10 minutes this tag-along stranger returns to see what the problem is. (nice chap) He can't figure it out either, so with time wasting my buddy and our new found friend take off to the local Harley shop before it closes to get them to bring a trailer for pick-up service. They arrive to a closed shop, but find about 20 riders who had just visited the shop prior to it closing for the day.
I'm sitting at the side of the road with my beloved Heritage for an hour or so wondering what happened to them, and all of a sudden over the hill comes what can only be described as the cavalry - my buddy, our new friend, and 20 or so others to assist anyway they can! Isn't the Harley family wonderful?
After another 20 minutes of everyone taking a stab at what the problem could be, with no positive results, one guy walks to the front left side of the bike, looks down just inside the left floorboard and pushes on a little plug... "Try it now" he says. I did and she fired up as good as ever!
The next day I went to the Harley shop to purchase a $2.70 clip to hold my alternator plug in place. The boys at the shop informed me that it is a common problem with them vibrating loose, so the clip is a very good investment. If it was that common, my question was... Why didn't all bikes come standard with the $2 clip for goodness sake?
Never had a problem since and that stranger has been a wonderful riding buddy for the past 20+ years.
Not sure if your year of bike is the same set-up because I know they did eventually change things to avoid this problem, but I though it was worth sharing my story with you. I hope it helps and your problem is as simple as mine.
Here's a picture of the clip and plug on my beloved '91 that still gets ridden occasionally.
Best of luck!
Mike