Scott:
In the midst of this stuff...what grade of gas is in it? Is it Regular, or is it some higher octane? It should be Regular with today's fuels, as they burn much slower than the fuels of old. I run Regular for everything except Interstate riding, anymore. The slower-burning fuels leave wetted surfaces in the 500/550 (and less so in the 350f/400f, but enough) intake, especially with any spitback issues, leading directly to over-fueled idle situations. The waste-spark cycle, if the timing advances too far at lower engine speeds, makes this real bad in the 500/550 in particular. Spitback wets the intake tract, directly causing hanging idle and sluggish performance below about 5k RPM.
In all of these engines, I have found that the starting angle (timing marks) must be on the "F" for each side below 1000 RPM. If it is not, the idle will hang on most of them, regardless of weak/strong spring issues for the advancers. When electronic triggers then get fitted, whatever timing advance you get at 3500+ RPM is what you get: there isn't much that can be done about that because of the way they work. If it is more than the normal full advance there will be a flat spot around 4000 RPM while the carbs and cam argue with each other for a bit, above that it straightens out again, much like a fixed-advance racing engine does. If it doesn't advance all the way above 3500 RPM then the gap of the electronic triggers is the issue, because the magnet(s) take some time to trigger those sensors. On those electronic units where the timing cannot be individually adjusted for the 1-4 and 2-3 sides, trouble is almost guaranteed. The old Marktek was famous for this latter feature, as were the older (but sadly more reliable?) Dyna S devices.