I've owned 5 RoadStars, some with the mileage pushed up pretty high, and I can feel confident saying that what you are experiencing is not typical steering behavior for a "maintained" RoadStar. I've also owned my fair share of late model Harley FLH's, and this problem is fairly typical with those bikes, even when new.
The HD tech's are directed to look for the obvious cause(s) first. This process will encompass, along with a thorough visual inspection, checking for: loose or missing hardware, unusual tire wear, low or high tire pressure, bent rim, proper spoke tension, out of balance wheel, wheel bearing issues, head bearing issue, nothing bent, broken...etc. The tech will do this for both the front, and the rear of the motorcycle. As odd as this may sound, loose/worn swing-arm bearings can cause a number of strange handling symptoms also.
If you don't want your favorite Yamaha shop to begin this process at $85.00hr, it is definitely worth giving it a try on your own. This will actually get you more familiar with your new ride and, who knows, you may discover the problem and have the unique satisfaction of repairing the bike on your own. Let us know how you make out.