Myself being a millennial-ish. Born in 1993 I look around at a lot of new motorcycles and there are truly some terrific deals on the market. I think the FZ-09 is a great price at what 8,000 brand new? There are midrange bikes that are considered more street and less rocket where you sit up a little straighter so its more casual. I have a 919 Hornet and absolutely love the bike because I can sit up pretty straight on it and ride with my head high.
The biggest problem is, is that even with great deals on new bikes most people are going to want a cruiser, and for what you get with a cruiser I believe they're over priced. The 2018 YZF-R3 looks like a hell of a bike and its only 4,999 while the cheapest cruiser is the lousy V-Star 250 at 4,400.
Nobody my age could afford to start on a 5,000 dollar motorcycle that they're probably going to outgrow after a season. It makes much more sense to buy used, and most friends I've tried to convert give up after awhile