Update: had the fork seals replaced today and was pleasantly surprised with 2 aspects of the job:
1. It cost significantly less than i was quoted. i was quoted $250 which mind you was far lower than some other dealers who quoted upwards of $400. In the end i only paid $160 for the job and it was done under 1.5 hours
2. The handling definitely seems improved now and it feels much more planted in the corners
It still seems like there is a bit of front-end turbulence below 50mph and the only thing left that hasn't been addressed is the front tire. The issue seems less pronounced than before the seals were replaced though and not as big a deal as it was originally. I'm guessing that the bike sat in the same position for several months between when the tire was new in Nov 2019 to when it was sold to me mid-March of this year and perhaps picked up some irregularity or flat spot as a result.
On another note, it rained pretty hard on the ride back and its so much better than previous non-fairing non-windscreened bikes and i got only lightly wet in some areas vs being completely soaked im sure if i had been riding my former chopper. Also, its 10x faster to clean up than former cruisers which were a nightmare to clean after a rain ride; with the R its a quick dry down and shiny as new :)