1st HD was a rigid Sporty bobber ('95 1200 & a weld-on rigid back half); loved it for what it was and rode the hell out of it. Not surprisingly, I (and my kidneys) wanted a bit more comfort, so I picked up a Breakout. I put many miles on the breakout, but for whatever reason forward controls kill my feet on longer trips. So, I decided to trade up to a Road King. The King is a great bike, but I kind of wanted a frame-mounted fairing for the occasional ride in high winds. Plus, after my wife's first >100 mile trip, she decided that I needed a tour pack with a nice, comfy back rest.
Long story short, it made more sense to just upgrade vs. adding all the needed accessories to the King. So, 2 days ago I traded up to a used '17 FLTRU in Black Quartz...loving it so far. I'm still trying to get used to saddling-up with a tour pack in the way, and the hydraulic clutch is definitely new, but I'm getting the hang of it. One thing that I was pleasantly surprised about, was the power increase (butt dyno) of the M8. Even with the added weight of the bike, it's noticeably more powerful than the 103 of the King.
I haven't been in strong winds yet, but the moderate winds I have been in still have an effect on the bike (it always will, no matter what), but at least it doesn't steer me around anymore like the windshield "sail" on the King.
The Ultra is noticeably more comfortable (smoother ride) than the King. I can only guess this is a result of the added weight and the shocks since they share the same basic frame/suspension design (I assume the shocks are stock at this point).
I love the look of the fairing (both the main and the lowers), but don't care for the look with the tour pack on.
The stock "T-Rex" handlebars have GOT to go...not comfortable at all for me.
Definitely adding QD mount for the tour pack as it will only be on there when the wife and I are taking an extended ride. (Still trying to find a laydown/curved license plate mount that'll work with a bottom-shining taillamp lens - feel free to point me in the right direction if you know of one).
All in all, I may add more bikes to the stable in the future, but I don't think I'll ever need to "upgrade" again. (famous last words...)