I personally believe a shop manual should be a mandatory purchase when anyone buys a Harley. In fact, considering how overpriced Harley's are the manual should be thrown in for free. The other alternative would be to purchase a vehicle that doesn't require all this maintenance and repair and modification and more maintenance and more repair, etc.
I've never given that much thought to how Harley determines which fasteners they put on the "Critical Fastener" list, other than the obvious ones that hold the wheels and brakes on, but I assume the list is more to cover their butts in liability suits than a reflection of what they find to be constantly coming loose over time based on real statistics gathered from real bikes. I just find it so 1950's to have to worry about checking fasteners every 5000 miles when the materials and technology have existed for a very long time to make this stuff a non issue. I guess H-D has never heard of proper torque control in assembly, lock nuts, locking thread adhesives, etc.
Considering my own experiences as well as those I've read about here and elsewhere, I believe one could make the case that every fastener on a Harley should be checked on a regular basis, most importantly including immediately after taking delivery to catch all that stuff the factory and the "dealer prep" inspection missed. I've found many more loose fasteners that weren't on the list than I ever found that were on the list. As 2lane noted, anything that could cause your butt to land on the highway is probably fairly critical and deserves at least some attention. I believe it's a good idea to develop the habit of giving everything a good visual inspection when you wash the bike, and take the time to put a wrench on anything that doesn't look right. Then do a full check with wrenches at least once per riding season just to be sure.
It has also been my experience that this fastener checking is most critical in the first 1000 and 5000 mile services, as that is where substandard tightening from the factory will show up. If everything has maintained torque that long, I've never found anything to subsequently "loosen" on it's own, barring actual breakage of a part, unless it was removed during a repair and not retightened properly.
Jerry