No, these guys are great and know what they are talking about. The part they were not sure about is the ability of the dealership to still remap. Their actual suggestion was to at least investigate the matter before I purchase a $500-900 tuner
Forget about "the stage one downloads are too lean". Yes, they're lean, but not that much more than any other setup running closed-loop using the stock O2 sensors. I run closed-loop and recommend it be done whenever possible, especially if you intend to travel very much. If you'll always be using the same fuel it's not so important to run closed-loop.
Even if you could get a dealer to load a stage one calibration into your bike, you're not addressing the intake breathing and that's the major player in the downloads. On top of that, H-D
will not have a calibration download (very) suitable for any set of headpipes that they didn't make, and they'd have to be "street legal" to boot, which means for your bike they'd have a cat inside.
In short, based upon your stated plans, you'd be just as well off running your stock calibration as having an H-D "stage one download" installed. It's six of one and half a dozen of the other in terms of how the calibrations are unsuitable for your purposes.
I say the best money is currently spent on a TTS tuning kit with some cables. Do a few v-tune runs as comprehensively as you can and your bike will run very well indeed. You will quickly forget all about the ~$500.