I think there's a lot of things at play. Used to be and as most recently as the mid 00's, you could walk into a dealership and see a huge price range of bikes from $2K all the way to $20K+. Out on the used lot, it wasn't uncommon to see starter bikes for $1K say for a Savage 650/S40 which were numerous and plentiful. I think I remember reading that one of my previously owned bikes a 07 Shadow 1100 had a MSRP of around $6500. Nowadays that would be well over $10K most likely judging by Rebel pricing. They've just gotten so expensive to acquire and for most of us, motorcycles are toys and not a necessity. Add in the non-stop increase in the cost of literally everything and it just pushes people away as they have to focus on meeting their obligations.
Next, add in the fact that for the most part, most younger riders gravitate towards nakeds and sportbikes neither of which Victory had in their lineup. Every Victory is a cruiser of some variation and there's not a single bike to be found, that has mid-controls in the lineup. When you're young and dumb, you want speed. This is why sportbikes and nakeds are so popular with the younger crowd. The older you get, the more responsible you get, you typically will have a family that relies on you, and you realize it's about the journey and not necessarily just about speed. That's where Indian, Harley and Victory come in.
I've always viewed (right or wrong) that Victory was kind of like that cool uncle in that they always had beautiful paint jobs, and were just a cooler version of Harley. I've always wanted to own one but it's only been in the last couple of years where the prices finally got to a level I could afford for a toy. Prior to this, I had to look at Japanese bikes as their price range runs the gamut and Victorys were still hovering around the $8K-$10K mark outside of the V92s.
I'd be interested to know how many riders gravitated to Victory over Harley coming off other types of bikes and what the appeal of Victorys was to them. For me, it's the style, paint, and American-made aspect that I truly love about them. The performance is just a bonus. I've always said when someone has asked me for purchasing advice asking if a certain bike would be "fast enough", that as long as it does the speed limit of whatever roads you ride then it's fast enough. In other words, for this 46 year old married father of 3 boys, it's all about the look, feel, and sound that gets me. Speed is the least important thing to me on my list. Honestly, when I bought my Hammer, I didn't really realize it was a "muscle" cruiser per se. I just liked the look of it and thought it was beautiful with those red wheels and two-tone paint along with the sound of those Victory Performance Pipes.
Enjoyed that, and since you asked, I'll share my story. To start, I am a research kind of guy. Sometimes it might take me over a year or two to make a purchase. But, at the age of around 50, I was single again and with no responsibilities, so decided to try riding again like back in the 60's/70's. Loved it then and turned out I loved it at 50 also. Bought a Sabre (this was in 08) and it was beautiful with the orange ghost flames, lots of chrome and extras including matching paint hard bags, over sized carb jets, and appropriate tune. Like you said, cheap for all that it had and the low milage. Met my soon to be wife on that bike and we began to travel. Of course, the Sabre, while capable, was just too small for as far as we wanted to go, so I went to a place called Global Motor Sports. It was one of those really good used bike shops that had every kind of bike you could want at very good prices. The old couple that ran it were bikers and he never bought junk to resale. You could go in there and pick something that suited you and take it away for not a whole lot of money. Maybe 2000 up to 10000 dollars and for ten grand you were getting something like a very nice not so old Wing or Harley. I found a 2000 Nomad with several extras and low miles (under 5000) for 5000 dollars drive off. Bike suited us very well and with just few modifications (seat mostly) we used that one for 60 thousand miles of travel all over the place. But I wanted something with a bit more (protection, anti lock brakes, storage, etc.) so I got a rediculous deal on a newer and larger Nomad 2007 model. I added a Harley trunk, front lowers, full fairing with stereo and really nice amp and head unit set up , and we rode that one about another 20 thousand miles. But about the time I picked up the second Nomad, I was starting to notice the Victories. I wanted one, and liked everything I learned about them, but they didn't have a tour version. Then the vision and I looked at it, but when I saw the storage, I declined. I saw the Cross Country and really liked the press on it, but again, no tour package. Well, then it happened, 2012 and the CCT came out. Bingo. Everything I wanted and even more. So the search began. I found one for sale by a guy in Oklahoma, about 12 hours away from our home in Houston. He and his wife had made other plans about a year after they bought their Cross Country Tour and were in the midst of buying land, building a home and trying to sell another home. They were strapped and she gave the ultimatum to sell the bike. It was one year old, had just under 11K miles on it, and he was an aircraft mechanic. For starters, he ordered it with every factory accessory possible, fenders, chrome controls, stage one pipes and tune, kicker speakers, luggage racks on trunk and bags, pull back bars, and the list goes on. Out the door he paid 28 Thousand plus a little more. I bought it for 13500.00. Met him at the bank in OK. and handed him a check. Oh, I mentioned his profession because he also "fixed" several issues that these bike had from the factory. Like the shift star, better 40 amp fuse, and I can't remember what else, but it was lacking only one more thing and I took care of that a few years later with cams and tune. And, I sold the newer Nomad for exactly what I had in it including the original cost plus all the extras I added even including the paint matching I had done. Still have the cross country with around 58K miles on it and it runs fantastic. It will be my last as I'm keeping it till one of us quits.
But, as you said, the shops like the one I got my first Nomad from are no more, and you can't just go to a place that has a showroom full of bikes from every type and age and range, yet still with good and reasonable prices. I miss that. There was another shop like Global on the south side of Houston I used to go into and look around. Loved being able to do that. They had two of the older really Nice Runes for sale with low miles for around 5 to 6 grand each. Wish I'd have bought them then.